Compendium of Organic Synthetic Methods, Volume 13 E-Book

Michael B. Smith

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Serie: Compendium of Organic Synthetic Methods
• Sprache: Englisch

Seitenzahl: 418

Veröffentlichungsjahr: 2014

Beschreibung

The Compendium of Organic Synthetic Methods serves as a handy desktop reference for organic chemists to browse new reactions and transformations of interest, facilitating the search for functional group transformations in the original literature of organic chemistry. Volume 13 contains both functional group transformations and carbon-carbon bond forming reactions from the literature in the years 2005-8. It presents examples of published reactions for the preparation of monofunctional compounds.

The Compendium of Organic Synthetic Methods series facilitates the search for quality, selected functional group transformations, organized by reacting functional group of starting material and functional group formed, with full references to each reaction
Presents examples of published reactions for the preparation of monofunctional compounds from the literature of 2005-8
Provides a handy reference and a valuable tool to the working organic chemist, allowing a quick check of known organic transformations
Stringent criteria for inclusion of reactions, including real synthetic utility of reactions, reagents readily available or easily prepared and handled in the laboratory

Leseprobe

Contents

Cover

Half Title page

Title page

Copyright page

Preface

Introduction

Index, Monofunctional Compounds

Index, Difunctional Compounds

Abbreviations

About the Author

Chapter 1: Preparation of Alkynes

Section 1: Alkynes from Alkynes

Section 2: Alkynes from Acid Derivatives

Section 3: Alkynes from Alcohols and Thiols

Section 4: Alkynes from Aldehydes

Section 5: Alkynes from Alkyls, Methylenes, and Aryls

Section 6: Alkynes from Amides

Section 7: Alkynes from Amines

Section 8: Alkynes from Esters

Section 9: Alkynes from Ethers, Epoxides, and Thioethers

Section 10: Alkynes from Halides and Sulfonates

Section 11: Alkynes from Hydrides

Section 12: Alkynes from Ketones

Section 13: Alkynes from Nitriles

Section 14: Alkynes from Alkenes

Section 15: Alkynes from Miscellaneous Compounds

Section 15A: Protection of Alkynes

Chapter 2: Preparation of Acid Derivatives

Section 16: Acid Derivatives from Alkynes

Section 17: Acid Derivatives from Acid Derivatives

Section 18: Acid Derivatives from Alcohols and Thiols

Section 19: Acid Derivatives from Aldehydes

Section 20: Acid Derivatives from Alkyls, Methylenes, and Aryls

Section 21: Acid Derivatives from Amides

Section 22: Acid Derivatives from Amines

Section 23: Acid Derivatives from Esters

Section 24: Acid Derivatives from Ethers, Epoxides, and Thioethers

Section 25: Acid Derivatives from Halides and Sulfonates

Section 26: Acid Derivatives from Hydrides

Section 27: Acid Derivatives from Ketones

Section 28: Acid Derivatives from Nitriles

Section 29: Acid Derivatives from Alkenes

Section 30: Acid Derivatives from Miscellaneous Compounds

Section 30A: Protection of Carboxylic Acid Derivatives

Chapter 3: Preparation of Alcohols

Section 31: Alcohols and Thiols from Alkynes

Section 32: Alcohols and Thiols from Acid Derivatives

Section 33: Alcohols and Thiols from Alcohol and Thiols

Section 34: Alcohols and Thiols from Aldehydes

Section 34A: Reductions of Aldehydes to Alcohols

Section 34B: Alkylation of Aldehydes, Forming Alcohols

Section 35: Alcohols and Thiols from Alkyls, Methylenes, and Aryls

Section 36: Alcohols and Thiols from Amides

Section 37: Alcohols and Thiols from Amines

Section 38: Alcohols and Thiols from Esters

Section 39: Alcohols and Thiols from Ethers, Epoxides, and Thioethers

Section 40: Alcohols and Thiols from Halides and Sulfonates

Section 41: Alcohols and Thiols from Hydrides

Section 42: Alcohols and Thiols from Ketones

Section 42A: Reduction of Ketones to Alcohols

Section 42B: Alkylation of Ketones, Forming Alcohols

Section 43: Alcohols and Thiols from Nitriles

Section 44: Alcohols and Thiols from Alkenes

Section 45: Alcohols and Thiols from Miscellaneous Compounds

Section 45A: Protection of Alcohols and Thiols

Chapter 4: Preparation of Aldehydes

Section 46: Aldehydes from Alkynes

Section 47: Aldehydes from Acid Derivatives

Section 48: Aldehydes from Alcohols and Thiols

Section 49: Aldehydes from Aldehydes

Section 50: Aldehydes from Alkyls, Methylenes, and Aryls

Section 51: Aldehydes from Amides

Section 52: Aldehydes from Amines

Section 53: Aldehydes from Esters

Section 54: Aldehydes from Ethers, Epoxides, and Thioethers

Section 55: Aldehydes from Halides and Sulfonates

Section 56: Aldehydes from Hydrides

Section 57: Aldehydes from Ketones

Section 58: Aldehydes from Nitriles

Section 59: Aldehydes from Alkenes

Section 60: Aldehydes from Miscellaneous Compounds

Section 60A: Protection of Aldehydes

Chapter 5: Preparation of Alkyls, Methylenes, and Aryls

Section 61: Alkyls, Methylenes, and Aryls from Alkynes

Section 62: Alkyls, Methylenes, and Aryls from Acid Derivatives

Section 63: Alkyls, Methylenes, and Aryls from Alcohols and Thiols

Section 64: Alkyls, Methylenes, and Aryls from Aldehydes

Section 65: Alkyls, Methylenes, and Aryls from Alkyls, Methylenes, and Aryls

Section 66: Alkyls, Methylenes, and Aryls from Amides

Section 67: Alkyls, Methylenes, and Aryls from Amines

Section 68: Alkyls, Methylenes, and Aryls from Esters

Section 69: Alkyls, Methylenes, and Aryls from Ethers, Epoxides, and Thioethers

Section 70: Alkyls, Methylenes, and Aryls from Halides and Sulfonates

Section 71: Alkyls, Methylenes, and Aryls from Hydrides

Section 72: Alkyls, Methylenes, and Aryls from Ketones

Section 73 Alkyls, Methylenes, and Aryls from Nitriles

Section 74: Alkyls, Methylenes and Aryls from Alkenes

Section 74A: Reduction of Alkene (and Aryl) Units

Section 74B: FORMATION of Aryls and Heteroaryls

Section 74C: Alkylations and Arylations of Alkenes

Section 74D: Conjugate Reduction of α,β-Unsaturated Carbonyl Compounds and Nitriles

Section 74E: Conjugate Alkylations

Section 74F: Formation of Three-Membered Rings from Alkenes

Section 74G: Formation of Four-Membered Rings

Section 75: Alkyls, Methylenes, and Aryls from Miscellaneous Compounds

Chapter 6: Preparation of Amides

Section 76: Amides from Alkynes

Section 77: Amides from Acids and Acid Derivatives

Section 78: Amides from Alcohols and Thiols

Section 79: Amides from Aldehydes

Section 80: Amides from Alkyls, Methylenes, and Aryls

Section 81: Amides from Amides

Section 82: Amides from Amines

Section 83: Amides from Esters

Section 84: Amides from Ethers, Epoxides, and Thioethers

Section 85: Amides from Halides and Sulfonates

Section 86: Amides from Hydrides

Section 87: Amides from Ketones

Section 88: Amides from Nitriles

Section 89: Amides from Alkenes

Section 90: Amides from Miscellaneous Compounds

Section 90A: Protection of Amides

Chapter 7: Preparation of Amines

Section 91: Amines from Alkynes

Section 92: Amines from Acid Derivatives

Section 93: Amines from Alcohols and Thiols

Section 94: Amines from Aldehydes

Section 95: Amines from Alkyls, Methylenes, and Aryls

Section 96: Amines from Amides

Section 97: Amines from Amines

Section 97A: Alkylation or Reduction of Imines and Related Compounds

Section 98: Amines from Esters

Section 99: Amines from Ethers, Epoxides, and Thioethers

Section 100: Amines from Halides and Sulfonates

Section 101: Amines from Hydrides

Section 102: Amines from Ketones

Section 103: Amines from Nitriles

Section 104: Amines from Alkenes

Section 105: Amines from Miscellaneous Compounds

Section 105A: Protection of Amines

Chapter 8: Preparation of Esters

Section 106: Esters from Alkynes

Section 107: Esters from Acid Derivatives

Section 108: Esters from Alcohols and Thiols

Section 109: Esters from Aldehydes

Section 110: Esters from Alkyls, Methylenes and Aryls

Section 111: Esters from Amides

Section 112: Esters from Amines

Section 113: Esters from Esters

Section 114: Esters from Ethers, Epoxides, and Thioethers

Section 115: Esters from Halides and Sulfonates

Section 116: Esters from Hydrides

Section 117: Esters from Ketones

Section 118: Esters from Nitriles

Section 119: Esters from Alkenes

Section 120: Esters from Miscellaneous Compounds

Chapter 9: Preparation of Ethers, Epoxides, and Thioethers

Section 121: Ethers, Epoxides, and Thioethers from Alkynes

Section 122: Ethers, Epoxides, and Thioethers from Acid Derivatives

Section 123: Ethers, Epoxides, and Thioethers from Alcohols and Thiols

Section 124: Ethers, Epoxides, and Thioethers from Aldehydes

Section 125: Ethers, Epoxides, and Thioethers from Alkyls, Methylenes, and Aryls

Section 126: Ethers, Epoxides, and Thioethers from Amides

Section 127: Ethers, Epoxides, and Thioethers from Amines

Section 128: Ethers, Epoxides, and Thioethers from Esters

Section 129: Ethers, Epoxides, and Thioethers from Ethers, Epoxides, and Thioethers

Section 130: Ethers, Epoxides, and Thioethers from Halides and Sulfonates

Section 131: Ethers, Epoxides, and Thioethers from Hydrides

Section 132: Ethers, Epoxides, and Thioethers from Ketones

Section 133: Ethers, Epoxides, and Thioethers from Nitriles

Section 134: Ethers, Epoxides, and Thioethers from Alkenes

Section 135: Ethers, Epoxides, and Thioethers from Miscellaneous Compounds

Chapter 10: Preparation of Halides and Sulfonates

Section 136: Halides and Sulfonates from Alkynes

Section 137: Halides and Sulfonates from Acid Derivatives

Section 138: Halides and Sulfonates from Alcohols and Thiols

Section 139: Halides and Sulfonates from Aldehydes

Section 140: Halides and Sulfonates from Alkyls, Methylenes, and Aryls

Section 141: Halides and Sulfonates from Amides

Section 142: Halides and Sulfonates from Amines

Section 143: Halides and Sulfonates from Esters

Section 144: Halides and Sulfonates from Ethers, Epoxides, and Thioethers

Section 145: Halides and Sulfonates from Halides and Sulfonates

Section 146: Halides and Sulfonates from Hydrides

Section 147: Halides and Sulfonates from Ketones

Section 148: Halides and Sulfonates from Nitriles

Section 149: Halides and Sulfonates from Alkenes

Section 150: Halides and Sulfonates from Miscellaneous Compounds

Chapter 11: Preparation of Hydrides

Section 151: Hydrides from Alkynes

Section 152: Hydrides from Acid Derivatives

Section 153: Hydrides from Alcohols and Thiols

Section 154: Hydrides from Aldehydes

Section 155: Hydrides from Alkyls, Methylenes, and Aryls

Section 156: Hydrides from Amides

Section 157: Hydrides from Amines

Section 158: Hydrides from Esters

Section 159: Hydrides from Ethers, Epoxides, and Thioethers

Section 160: Hydrides from Halides and Sulfonates

Section 161: Hydrides from Hydrides

Section 162: Hydrides from Ketones

Section 163: Hydrides from Nitriles

Section 164: Hydrides from Alkenes

Section 165: Hydrides from Miscellaneous Compounds

Chapter 12: Preparation of Ketones

Section 166: Ketones from Alkynes

Section 167: Ketones from Acid Derivatives

Section 168: Ketones from Alcohols and Thiols

Section 169: Ketones from Aldehydes

Section 170: Ketones from Alkyls, Methylenes, and Aryls

Section 171: Ketones from Amides

Section 172: Ketones from Amines

Section 173: Ketones from Esters

Section 174: Ketones from Ethers, Epoxides, and Thioethers

Section 175: Ketones from Halides and Sulfonates

Section 176: Ketones from Hydrides

Section 177: Ketones from Ketones

Section 178: Ketones from Nitriles

Section 179: Ketones from Alkenes

Section 180: Ketones from Miscellaneous Compounds

Section 180A: Protection of Ketones

Chapter 13: Preparation of Nitriles

Section 181: Nitriles from Alkynes

Section 182: Nitriles from Acid Derivatives

Section 183: Nitriles from Alcohols and Thiols

Section 184: Nitriles from Aldehydes

Section 185: Nitriles from Alkyls, Methylenes, and Aryls

Section 186: Nitriles from Amides

Section 187: Nitriles from Amines

Section 188: Nitriles from Esters

Section 189: Nitriles from Ethers, Epoxides, and Thioethers

Section 190: Nitriles from Halides and Sulfonates

Section 191: Nitriles from Hydrides

Section 192: Nitriles from Ketones

Section 193: Nitriles from Nitriles

Section 194: Nitriles from Alkenes

Section 195: Nitriles from Miscellaneous Compounds

Chapter 14: Preparation of Alkenes

Section 196: Alkenes from Alkynes

Section 197: Alkenes from Acid Derivatives

Section 198: Alkenes from Alcohols and Thiols

Section 199: Alkenes from Aldehydes

Section 200: Alkenes from Alkyls, Methylenes, and Aryls

Section 201: Alkenes from Amides

Section 202: Alkenes from Amines

Section 203: Alkenes from Esters

Section 204: Alkenes from Ethers, Epoxides, and Thioethers

Section 205: Alkenes from Halides and Sulfonates

Section 206: Alkenes from Hydrides

Section 207: Alkenes from Ketones

Section 208: Alkenes from Nitriles

Section 209: Alkenes from Alkenes

Section 210: Alkenes from Miscellaneous Compounds

Chapter 15: Preparation of Oxides

Section 211: Oxides from Alkynes

Section 212: Oxides from Acid Derivatives

Section 213: Oxides from Alcohols and Thiols

Section 214: Oxides from Aldehydes

Section 215: Oxides from Alkyls, Methylenes, and Aryls

Section 216: Oxides from Amides

Section 217: Oxides from Amines

Section 218: Oxides from Esters

Section 219: Oxides from Ethers, Epoxides, and Thioethers

Section 220: Oxides from Halides and Sulfonates

Section 221: Oxides from Hydrides

Section 222: Oxides from Ketones

Section 223: Oxides from Nitriles

Section 224: Oxides from Alkenes

Section 225: Oxides from Miscellaneous Compounds

Chapter 16: Preparatation of Difunctional Compounds

Section 300: Alkyne - Alkyne

Section 301: Alkyne - Acid Derivatives

Section 302: Alkyne - Alcohol, Thiol

Section 303: Alkyne - Aldehyde

Section 304: Alkyne - Amide

Section 305: Alkyne - Amine

Section 306: Alkyne - Ester

Section 307: Alkyne - Ether, Epoxide, Thioether

Section 308: Alkyne - Halide

Section 309: Alkyne - Ketone

Section 310: Alkyne - Nitrile

Section 311: Alkyne - Alkene

Section 312: Carboxylic Acid - Carboxylic Acid

Section 313: Carboxylic Acid - Alcohol, Thiol

Section 314: Carboxylic Acid - Aldehyde

Section 315: Carboxylic Acid - Amide

Section 316: Carboxylic Acid - Amine

Section 317: Carboxylic Acid - Ester

Section 318: Carboxylic Acid - Ether, Epoxide, Thioether

Section 319: Carboxylic Acid - Halide, Sulfonate

Section 320: Carboxylic Acid - Ketone

Section 321: Carboxylic Acid - Nitrile

Section 322: Carboxylic Acid - Alkene

Section 323: Alcohol, Thiol - Alcohol, Thiol

Section 324: Alcohol, Thiol - Aldehyde

Section 325: Alcohol, Thiol - Amide

Section 326: Alcohol, Thiol - Amine

Section 327: Alcohol, Thiol - Ester

Section 328: Alcohol, Thiol - Ether, Epoxide, Thioether

Section 329: Alcohol, Thiol - Halide, Sulfonate

Section 330: Alcohol, Thiol - Ketone

Section 331: Alcohol, Thiol - Nitrile

Section 332: Alcohol, Thiol - Alkene

Section 333: Aldehyde - Aldehyde

Section 334: Aldehyde - Amide

Section 335: Aldehyde - Amine

Section 336: Aldehyde - Ester

Section 337: Aldehyde - Ether, Epoxide, Thioether

Section 338: Aldehyde - Halide, Sulfonate

Section 339: Aldehyde - Ketone

Section 340: Aldehyde - Nitrile

Section 341: Aldehyde - Alkene

Section 342: Amide - Amide

Section 343: Amide - Amine

Section 344: Amide - Ester

Section 345: Amide - Ether, Epoxide, Thioether

Section 346: Amide - Halide, Sulfonate

Section 347: Amide - Ketone

Section 348: Amide - Nitrile

Section 349: Amide - Alkene

Section 350: Amine - Amine

Section 351: Amine - Ester

Section 352: Amine - Ether, Epoxide, Thioether

Section 353: Amine - Halide, Sulfonate

Section 354: Amine - Ketone

Section 355: Amine - Nitrile

Section 356: Amine - Alkene

Section 357: Ester - Ester

Section 358: Ester - Ether, Epoxide, Thioether

Section 359: Ester - Halide, Sulfonate

Section 360: Ester - Ketone

Section 361: Ester - Nitrile

Section 362: Ester - Alkene

Section 363: Ether, Epoxide, Thioether - Ether, Epoxide, Thioether

Section 364: Ether, Epoxide, Thioether - Halide, Sulfonate

Section 365: Ether, Epoxide, Thioether - Ketone

Section 366: Ether, Epoxide, Thioether - Nitrile

Section 367: Ether, Epoxide, Thioether - Alkene

Section 368: Halide, Sulfonate - Halide, Sulfonate

Section 369: Halide, Sulfonate - Ketone

Section 370: Halide, Sulfonate - Nitrile

Section 371: Halide, Sulfonate - Alkene

Section 372: Ketone - Ketone

Section 373: Ketone - Nitrile

Section 374: Ketone - Alkene

Section 375: Nitrile - Nitrile

Section 376: Nitrile - Alkene

Section 377: Alkene - Alkene

Section 378: Oxides - Alkynes

Section 379: Oxides - Acid Derivatives

Section 380: Oxides - Alcohols, Thiols

Section 381: Oxides - Aldehydes

Section 382: Oxides - Amides

Section 383: Oxides - Amines

Section 384: Oxides - Esters

Section 385: Oxides - Ethers, Epoxides, Thioethers

Section 386: Oxides - Halides, Sulfonates

Section 387: Oxides - Ketones

Section 388: Oxides - Nitriles

Section 389: Oxides - Alkenes

Section 390: Oxides - Oxides

Index

Compendium of Organic Synthetic Methods

Copyright © 2014 by John Wiley & Sons, Inc. All rights reserved.

Published by John Wiley & Sons, Inc., Hoboken, New Jersey. All rights reserved.Published simultaneously in Canada.

No part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, scanning, or otherwise, except as permitted under Section 107 or 108 of the 1976 United States Copyright Act, without either the prior written permission of the Publisher, or authorization through payment of the appropriate per-copy fee to the Copyright Clearance Center, Inc., 222 Rosewood Drive, Danvers, MA 01923, [phone], fax [phone], or on the web at www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, [phone], fax [phone], or online at http://www.wiley.com/go/permission.

Limit of Liability/Disclaimer of Warranty: While the publisher and author have used their best efforts in preparing this book, they make no representations or warranties with respect to the accuracy or completeness of the contents of this book and specifically disclaim any implied warranties of merchantability or fitness for a particular purpose. No warranty may be created or extended by sales representatives or written sales materials. The advice and strategies contained herein may not be suitable for your situation. You should consult with a professional where appropriate. Neither the publisher nor author shall be liable for any loss of profit or any other commercial damages, including but not limited to special, incidental, consequential, or other damages.

For general information on our other products and services or for technical support, please contact our Customer Care Department within the United States at [phone], outside the United States at [phone] or fax [phone].

Wiley also publishes its books in a variety of electronic formats. Some content that appears in print may not be available in electronic format. For information about Wiley products, visit our web site at www.wiley.com.

Library of Congress Cataloging-in-Publication Data is available.

978-1-118-79168-4

PREFACE

Since the original volume in this series by Ian and Shuyen Harrison, the goal of the Compendium of Organic Synthetic Methods has been to facilitate the search for functional group transformations in the original literature of organic chemistry. In Volume 2, difunctional compounds were added, and this compilation was continued by Louis Hegedus and Leroy Wade for Volume 3 of the series. Professor Wade became the author for Volume 4 and continued with Volume 5. I began editing the series with Volume 6, where I introduced an author index for the first time and added a new chapter (Chapter 15, Oxides). Volume 7 introduced Section 378 (Oxides-Alkynes) through Section 390 (Oxides-Oxides). The Compendium is a handy desktop reference that remains a valuable tool to the working organic chemist, allowing a quick check of the literature. Even in the era of powerful computer searching, the Compendium allows one to “browse” for new reactions and transformations that may be of interest in a rapid and logical manner. The body of organic chemistry literature is very large and the Compendium is a focused and highly representative survey of the literature, and is offered in that context.

Compendium of Organic Synthetic Methods, Volume 13 contains both functional group transformations and carbon-carbon bond-forming reactions from the literature appearing in the years 2005, 2006, 2007, and 2008. The classification schemes used for Volumes 6–12 have been continued. Difunctional compounds appear in Chapter 16. The experienced user of the Compendium will require no special instructions for the use of Volume 13. The has been continued as in Volumes 6–12.

Every effort has been made to keep the manuscript error-free. Where there are errors, I take full responsibility. If there are questions or comments, the reader is encouraged to contact me directly at the address, phone, fax, or email given below.

As I have done throughout my writing career, I thank my wife, Sarah, and my son, Steven, for their encouragement and support during this work. I also thank Jonathan Rose of Wiley for his help in the publication of this volume.

Michael B. Smith

Department of Chemistry, University of Connecticut55 N. Eagleville RoadStorrs, Connecticut 06269-3060

Voice phone:    [phone]        Fax:    [phone]Email:        [email protected]

Storrs, ConnecticutDecember, 2013

INTRODUCTION

Relationship Between Volume 13 and Previous Volumes. Compendium of Organic Synthetic Methods, Volume 13 presents more than 2550 examples of published reactions for the preparation of monofunctional compounds, updating the more than 18,000 examples found in Volumes 1–12. Volume 13 contains about 1000 examples of reactions that prepare difunctional compounds with various functional groups, updating the more than 10,000 examples in Volumes 1–12. Reviews have long been a feature of this series, and Volume 13 adds 99 pertinent reviews in the various sections.

Chapters 1–14 present the same functional group transformations as found in Volumes 1–12, as does Chapter 15, introduced in Volume 6. Difunctional compounds appear in Chapter 16, as in Volumes 6–12. The sections on oxides as part of difunctional compounds, introduced in volume 7, continues in Chapter 16 of Volumes 8–12 with Section 378 (Oxides-Alkynes) through Section 390 (Oxides-Oxides).

Following Chapter 16 is a complete alphabetical listing of all authors (last name, initials). The authors along with the pertinent reference are listed for each citation below the reaction.

Classification and Organization of Reactions Forming Monofunctional Compounds. Chemical transformations are classified according to the reacting functional group of the starting material and the functional group formed. Those reactions that give products with the same functional group form a chapter. The reactions in each chapter are further classified into sections on the basis of the functional group of the starting material. Within each section, reactions are arranged by year: 2008 reactions are listed first, followed by 2007, 2006, and then reactions from 2005. Review articles are collected at the end of each appropriate section.

The classification is unaffected by allylic, vinylic, or acetylenic unsaturation appearing in both starting material and product, or by increases or decreases in the length of carbon chains; for example, the reactions t-BuOH → t-BuCOOH, PhCH2OH → PhCOOH, and PhCH=CHCH2OH → PhCH=CHCOOH would all be considered as preparations of carboxylic acids from alcohols. Sections 74D (Alkyls from Alkenes: Conjugate Reductions) and 74E (Alkyls from Alkenes; Conjugate Alkylations) contain the reactions conjugate reduction or conjugate alkylation of unsaturated ketones, aldehydes, esters, acids, and nitriles, respectively.

The terms hydrides, alkyls, and aryls classify compounds containing reacting hydrogen atoms, alkyl groups, and aryl groups, respectively; for example, RCH2-H → RCH2COOH (carboxylic acids from hydrides), RMe → RCOOH (carboxylic acids from alkyls), RPh → RCOOH (carboxylic acids from aryls). Note the distinction between R2CO → R2CH2 (methylenes from ketones) and RCOR’ → RH (hydrides from ketones). Alkylations involving additions across double bonds are given in Section 74 (Alkyls, Methylenes, and Aryls from Alkenes).

The following examples illustrate the classification of some potentially contusing cases:

How to Use the Book to Locate Examples of the Preparation of Protection of Monofunctional Compounds. Examples of the preparation of one functional group from another are given in the monofunctional index on p. xi, which lists the corresponding section and page. Sections that contain examples of the reactions of a functional group are given in the horizontal rows of this index. Section 1 gives examples of the reactions of alkynes that form new alkynes; Section 16 gives reactions of alkynes that form carboxylic acids; and Section 31 gives reactions of acetylenes that form alcohols.

Note that Chapter 2 presents reactions that form carboxylic acids, but reactions that form acid halides or acid anhydrides are also listed. Reactions that form amides are presented in Chapter 6 and reactions that form esters are presented in Chapter 8.

Examples of alkylation, dealkylation, homologation, isomerization, and transposition are given in Sections 1,17, 33, and so on, lying close to a diagonal of the index. These sections correspond to such topics as the preparation of acetylenes from acetylenes; carboxylic acids from carboxylic acids; and alcohols, thiols, and phenols from alcohols, thiols, and phenols. Alkylations that involve conjugate additions across a double bond are given in Section 74E (Alkyls, Methylenes, and Aryls from Alkenes).

Examples of name reactions may be found by first considering the nature of the starting material and product. The Wittig reaction, for instance, is given in Section 199 (Alkenes from Aldehydes) and in Section 207 (Alkenes from Ketones). The aldol condensation may be found in the chapters on difunctional compounds in Section 324 (Alcohol, Thiol-Aldehyde) and in Section 330 (Alcohol, Thiol-Ketone). Examples of the synthetically important alkene metathesis reaction are provided primarily in Section 209 (Alkenes from Alkenes). Examples of the Heck reaction are presented in Section 74C, those for the Suzuki reaction in Section 70, and examples of the Sonogashira reaction are presented in Section 300.

Examples of the protection of acetylenes, carboxylic acids, alcohols, phenols, aldehydes, amides, amines, esters, ketones, and alkenes are also presented. Sections (designated with an A: 15A, 30A, etc.) are labeled “Protection of and are located at the end of pertinent chapters.

Some pairs of functional groups, such as alcohol, ester; carboxylic acid, ester; amine, amide; and carboxylic acid, amide, can be interconverted by simple reactions. When a member of these groups is the desired product or starting material, the other member should also be consulted in the text.

The original literature must be used to determine the generality of reactions. A reaction given in this book for a primary aliphatic substrate may also be applicable to tertiary or aromatic compounds. This book provides very limited experimental conditions or precautions and the reader is directed to the original literature before attempting a reaction. In no instance should a citation in this book be taken as a complete experimental procedure. Failure to refer to the original literature prior to beginning laboratory work could be hazardous. The original papers usually yield a further set of references to previous work. Papers that appear after those publications can usually be found by consulting SciFinder, or related search engines.

Classification and Organization of Reactions Forming Difunctional Compounds. This chapter considers all possible difunctional compounds formed from the groups acetylene, carboxylic acid, alcohol, thiol, aldehyde, amide, amine, ester, ether, epoxide, thioether, halide, ketone, nitrile, and alkene. Reactions that form difunctional compounds are classified into sections on the basis of two functional groups in the product that are pertinent to the reaction. The relative positions of the groups do not affect the classification. Thus preparations of 1,2-aminoalcohols, 1,3-aminoalcohols, and 1,4-aminoalcohols are included in a single section (Section 326, Alcohol, Thiol-Amine). Difunctional compounds that have an oxide as the second group may be found in the appropriate section (Sections 278–290). The nitroketone product of oxidation of a nitroalcohol is given in Section 384 (Ketone-Oxide). The product of a nitroaldol reaction is a nitro-alcohol, and examples are found in Section 380. Conversion of an oxide (such as nitro or a sulfone moiety) to another functional group is generally given in the Miscellaneous section of the sections concerning monofunctional compounds. Conversion of a nitroalkane to an amine, for example, is given in Section 105 (Amines from Miscellaneous Compounds).

The following examples illustrate applications of this classification system:

Difunctional Product

Section Title

RC≡C—C≡CR

Acetylene-Acetylene

RCH(OH)COOH

Carboxylic acid-Alcohol

RCH=CHOMe

Ether-Alkene

RCHF

2

Halide-Halide

RCH(Br)CH

2

F

Halide-Halide

RCH(OAc)CH

2

OH

Alcohol-Ester

RCH(OH)CO

2

Me

Alcohol-Ester

RCH=CHCH

2

CO

2

Me

Ester-Alkene

RCH=CHOAc

Ester-Alkene

RCH(OMe)CH

2

SO

2

CH

2

CH

2

OH

Alcohol-Ether

RSO

2

CH

2

CH

2

OH

Oxide-Alcohol

How to Use the Book to Locate Examples of the Preparation of Difunctional Compounds. The difunctional index on p. xvi gives the section and page corresponding to each difunctional product. Thus, Section 327 (Alcohol, Thiol-Ester) contains examples of the preparation of hydroxyesters; Section 323 (Alcohol, Thiol-Alcohol, Thiol) contains examples of the preparation of diols.

Some preparations of alkene and acetylenic compounds from alkene and acetylenic starting materials can, in principle, be classified in either the monofunctional or difunctional sections; for example, the transformation RCH=CHBr → RCH=CHCOOH could be considered as preparing carboxylic acids from halides (Section 25, monofunctional compounds) or as preparing a carboxylic acid-alkene (Section 322, difunctional compounds). The choice usually depends on the focus of the particular paper where this reaction appeared. In such cases both sections should be consulted.

Reactions applicable to both aldehyde and ketone starting materials are in many cases illustrated by an example that uses only one of them. Similarly, many citations for reactions found in the Aldehyde-X sections include examples that could be placed in the Ketone-X section. Again, the choice for categorizing these reactions is dictated by the original publication in which the reaction appeared.

Many literature preparations of difunctional compounds are extensions of the methods applicable to monofunctional compounds. As an example, the reaction RCl → ROH might be used for the preparation of diols from an appropriate dichloro compound. Such methods are difficult to categorize and may be found in either the monofunctional or difunctional sections, depending on the focus of the original paper.

The user should bear in mind that the pairs of functional groups alcohol, ester; carboxylic acids, ester; amine, amide; and carboxylic acid, amide can be interconverted by simple reactions. Compounds of the type RCH(OAc)CH2OAc (Ester-Ester) would thus be of interest to anyone preparing the diol RCH(OH)CH2OH (Alcohol-Alcohol).

INDEX, MONOFUNCTIONAL COMPOUNDS

INDEX, DIFUNCTIONAL COMPOUNDS

ABBREVIATIONS

ABOUT THE AUTHOR

Michael B. Smith is Professor of Chemistry in the Department of Chemistry at the University of Connecticut, at Storrs. His research interests focus on developing a indocyanine green derived dye-conjugate that targets hypoxic cancerous tumors. In addition, he is synthesizing a lipid-loaded dipeptide isolated from the dental pathogen Porphyromonas gingivalis that is involved in multiple sclerosis.

Professor Smith is also the author of Volumes 6–12 of the Compendium of Organic Synthetic Methods, the author of the 5th, 6th, and 7th editions of March’s Advanced Organic Chemistry, and the author of Organic Synthesis, 1st, 2nd, and 3rd editions as well as several monographs. Professor Smith is also the author of an undergraduate textbook, Organic Chemistry: An Acid-Base Approach, published by CRC Press.

Professor Smith received his Ph.D. in Organic Chemistry from Purdue University in 1977, a B.S. in Chemistry from Virginia Tech in 1969, and an A.A. from Ferrum College in 1967. He did postdoctoral work with Professor George R. Pettit at the Arizona State University and with Professor Sidney M. Hecht at the Massachusetts Institute of Technology.

CHAPTER 1

PREPARATION OF ALKYNES

SECTION 1: ALKYNES FROM ALKYNES

Rahaim, Jr., R.J.; Shaw, J.T. J. Org. Chem.2008, 73, 2912.

Huang, H.; Liu, H.; Jiang, H.; Chen, K. J. Org. Chem.2008, 73, 6037.

Moon, J.; Jeong, M.; Nam, H.; Ju, J.; Moon, J.H.; Jung, H-M.; Lee, S. Org. Lett.2008, 10, 945.

Xie, C.; Liu, L.; Zhang, Y.; Xu, P. Org. Lett.2008, 10, 2393.

Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem.2008, 73, 9061.

Monnier, F.; Turtaut, F.; Duroure, L.; Taillefer, M. Org. Lett.2008, 10, 3203.

Lipshutz, B.H.; Chung, D.W.; Rich, B. Org. Lett.2008, 10, 3793.

de Lima, P.G.; Antunes, O.A.C. Tetrahedron Lett.2008, 49, 2506.

Komáromi, A.; Tolnai, G.L.; Novák, Z. Tetrahedron Lett.2008, 49, 7294.

Uemura, M.; Yorimitsu, H.; Oshima, K. Tetrahedron2008, 64, 1829.

Mori, S.; Yanase, T.; Aoyagi, S.; Monguchi, Y.; Maegawa, T.; Sajiki, H. Chemistry: European J.2008, 14, 6994.

Tambade, P.J.; Patil, Y.P.; Nandurkar, N.S.; Bhanage, B.M. Synlett2008, 886.

de Souza, R.O.M.A.; Bittar, M.S.; Mendes, L.V.P.; da Silva, C.M.F.; da Silva, V.T.; Antunes, O.A.C. Synlett2008, 1777.

Nishihara, Y.; Inoue, E.; Okada, Y.; Takagi, K. Synlett2008, 3041.

Brown, W.S.; Boykin, D’A.D.; Sonnier, Jr., M.Q.; Clark, W.D.; Brown, F.V.; Shaughnessy, K.H. Synthesis2008, 1965.

Zhu, M.; Zhou, Z.; Chen, R. Synthesis2008, 2680.

Wu, M.; Mao, J.; Guo, J.; Ji, S. Eur. J. Org. Chem.2008, 4050.

Li, P.; Wang, L.; Wang, M.; You, F. Eur. J. Org. Chem.2008, 5946.

Tang, B.-X.; Wang, F.; Li, J.-H.; Xie, Y.-X.; Zhang, M.-B. J. Org. Chem.2007, 72, 6294.

DeRoy, P.L.; Surprenant, S.; Bertrand-Laperle, M.; Yoakim, C. Org. Lett.2007, 9, 2741.

Guan, J.T.; Weng, T.Q.; Yu, G.-A.; Liu, S.H. Tetrahedron Lett.2007, 48, 7129.

Cai, M.; Sha, J.; Xu, Q. Tetrahedron2007, 63, 4642.

Colacino, E.; Daïch, L.; Martinez, J.; Lamaty, F. Synlett2007, 1279.

Yi, W.-B.; Cai, C.; Wang, X. Eur. J. Org. Chem.2007, 3445.

Yang, F.; Wu, Y. Eur. J. Org. Chem.2007, 3476.

Chen, G.; Zhu, X.; Cai, J.; Wan, Y. Synth. Commun.2007, 37, 1355.

Ren, T.; Zhang, Y.; Zhu, W.; Zhou, J. Synth. Commun.2007, 37, 3279.

Zhao, Y.; Wang, H.; Hou, X.; Hu, Y.; Lei, A.; Zhang, H; Zhu, L. J. Am. Chem. Soc.2006, 128, 15048.

Liang, Y.; Xie, Y.-X.; Li, J.-H. J. Org. Chem.2006, 71, 379.

Yi, C.; Hua, R. J. Org. Chem.2006, 71, 2535.

Altenhoff, G.; Würtz, S.; Glorius, F. Tetrahedron Lett.2006, 47, 2925.

Cwik, A.; Hell, Z.; Figueras, F. Tetrahedron Lett.2006, 47, 3023.

Li, P.; Wang, L. Synlett2006, 2261.

Hierso, J.C.; Picquet, M.; Cattey, H.; Meunier, P. Synlett2006, 3005.

Deng, C.-L.; Xie, Y.-X.; Yin, D.-L,; Li, J.-H. Synthesis2006, 3370.

Torres, G.H.; Choppin, S.; Colobert, F. Eur. J. Org. Chem.2006, 1450.

Thathagar, M.B.; Rothenberg, G. Org. Biomol. Chem.2006, 4, 111.

Liang, B.; Dai, M.; Chen, J.; Yang, Z. J. Org. Chem.2005, 70, 391.

Nakamura, H.; Onagi, S.; Kamakura, T. J. Org. Chem.2005, 70, 2357.

Jiang, H.; Zhu, S. Tetrahedron Lett.2005, 46, 517.

Borah, H.N.; Prajapati, D.; Boruah, R.C. Synlett2005, 2823.

Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett.2005, 46, 1717.

Zhang, G. Synlett2005, 619.

Li, J.-H.; Zhang, X.-D.; Xie, Y.-X. Synthesis2005, 804.

Li, J.-H.; Zhang, X.-D.; Xie, Y.-X. Eur. J. Org. Chem.2005, 4256.

REVIEWS

“Alkyne Metathesis” Fürstner, A.; Davies, P.W. Chem. Commun.2005, 2307.

SECTION 2: ALKYNES FROM ACID DERIVATIVES

Arisawa, M.; Fujimoto, K.; Morinaka, S.; Yamaguchi, M. J. Am. Chem. Soc.2005, 127, 12226.

SECTION 3: ALKYNES FROM ALCOHOLS AND THIOLS

Sugai, T.; Itoh, A. Tetrahedron Lett.2007, 48, 9096.

Kabalka, G.W.; Yao, M.-L.; Borella, S. Org. Lett.2006, 8, 879.

SECTION 4: ALKYNES FROM ALDEHYDES

NO ADDITIONAL EXAMPLES

SECTION 5: ALKYNES FROM ALKYLS, METHYLENES, AND ARYLS

NO ADDITIONAL EXAMPLES

SECTION 6: ALKYNES FROM AMIDES

NO ADDITIONAL EXAMPLES

SECTION 7: ALKYNES FROM AMINES

NO ADDITIONAL EXAMPLES

SECTION 8: ALKYNES FROM ESTERS

Kabalka, G.W.; Naravane, A.; Zhao, L.L. Tetrahedron Lett.2007, 48, 7091.

SECTION 9: ALKYNES FROM ETHERS, EPOXIDES, AND THIOETHERS

NO ADDITIONAL EXAMPLES

SECTION 10: ALKYNES FROM HALIDES AND SULFONATES

Csékei, M.; Novák, Z.; Kotschy, A. Tetrahedron2008, 64, 975.

Zhang, W.; Wu, H.; Liu, Z.; Zhong, P.; Zhang, L.; Huang, X.; Cheng, J. Chem. Commun.2006, 4826.

Qian, M.; Negishi, E.-i. Tetrahedron Lett.2005, 46, 2927.

SECTION 11: ALKYNES FROM HYDRIDES

Seregin, I.V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc.2007, 129, 7742.

For examples of the reaction RC≡CH → RC≡C-C≡CR1, see Section 300 (Alkyne-Alkyne).

SECTION 12: ALKYNES FROM KETONES

Ghaffarzadeh, M.; Bolourtchian, M.; Fard, Z.H.; Halvagar, M.R.; Mohsenzadeh, F. Synth. Commun.2006, 36, 1973.

SECTION 13: ALKYNES FROM NITRILES

NO ADDITIONAL EXAMPLES

SECTION 14: ALKYNES FROM ALKENES

Shirakura, M.; Suginome, M. J. Am. Chem. Soc.2008, 130, 5410.

Chelucci, G.; Capitta, F.; Baldino, S.; Pinn, G.A. Tetrahedron Lett.2007, 48, 6514.

Okutani, M.; Mori, Y. Tetrahedron Lett.2007, 48, 6856.

Caporusso, A.M.; Zampieri, A.; Aronica, L.A.; Banti, D. J. Org. Chem.2006, 71, 1902.

Knöpfel, T.F.; Zarotti, P.; Ichikawa, T.; Carreira, E.M. J. Am. Chem. Soc.2005, 127, 9682.

SECTION 15: ALKYNES FROM MISCELLANEOUS COMPOUNDS

NO ADDITIONAL EXAMPLES

SECTION 15A: PROTECTION OF ALKYNES

Orsini, A.; Vitérisi, A.; Bodlenner, A.; Weibel, J.-M.; Pale, P. Tetrahedron Lett.2005, 46, 259.

CHAPTER 2

PREPARATION OF ACID DERIVATIVES

SECTION 16: ACID DERIVATIVES FROM ALKYNES

NO ADDITIONAL EXAMPLES

SECTION 17: ACID DERIVATIVES FROM ACID DERIVATIVES

Serieys, A.; Botuha, C.; Chemla, F.; Ferreira, F.; Pérez-Luna, A. Tetrahedron Lett.2008, 49, 5322.

SECTION 18: ACID DERIVATIVES FROM ALCOHOLS AND THIOLS

Hirano, J.-i.; Miyamoto, K.; Ohta, H. Tetrahedron Lett.2008, 49, 1217.

Mannam, S.; Sekar, G. Tetrahedron Lett.2008, 49, 2457.

Ballistreri, F.P.; Tomaselli, G.A.; Toscano, R.M. Tetrahedron Lett.2008, 49, 3291.

Grill, J.M.; Ogle, J.W.; Miller, S.A. J. Org. Chem.2006, 71, 9291.

Svetlakov, N.V.; Nikitin, V.G.; Nikolaeva, E.A. Russ. J. Org. Chem.2007, 43, 773.

Hirashima, S.-i.; Hashimoto, S.; Masaki, Y.; Itoh, A. Tetrahedron2006, 62, 7887.

Kuwabara, K.; Itoh, A. Synthesis2006, 1949.

Wang, J.; Yan, L.; Li, G.; Wang, X.; Ding, Y.; Suo, J. Tetrahedron Lett.2005, 46, 7023.

SECTION 19: ACID DERIVATIVES FROM ALDEHYDES

Cafiero, L.R.; Snowden, T.S. Org. Lett.2008, 10, 3853.

Lim, M.; Yoon, C.-M.; An, G.; Rhee, H. Tetrahedron Lett.2007, 48, 3835.

Hashemi, M.M.; Ghazanfari, D.; Ahmadibeni, Y.; Karimi-Jaberi, Z.; Ezabadi, A. Synth. Commun.2005, 35, 1103.

SECTION 20: ACID DERIVATIVES FROM ALKYLS, METHYLENES, AND ARYLS

Sugai, T.; Itoh, A. Tetrahedron Lett.2007, 48, 2931.

Hirashima, S.-i.; Itoh, A. Synthesis2006, 1757.

Gupta, M.; Paul, S.; Gupta, R.; Loupy, A. Tetrahedron Lett.2005, 46, 495.

SECTION 21: ACID DERIVATIVES FROM AMIDES

NO ADDITIONAL EXAMPLES

SECTION 22: ACID DERIVATIVES FROM AMINES

Naik, R.; Pasha, M.A. Synth. Commun.2006, 36, 165.

SECTION 23: ACID DERIVATIVES FROM ESTERS

Fotakopoulou, I.; Barbayianni, E.; Constantinou-Kokotou, V.; Bornscheuer, U.T.; Kokotos, G. J. Org. Chem.2007, 72, 782.

Goel, A.; Verma, D.; Dixit, M.; Raghunandan, R.; Maulik, P.R. J. Org. Chem.2006, 71, 804.

Lesma, G.; Sacchetti, A.; Silvani, A. Synthesis2006, 594.

Nishiguchi, A.; Maeda, K.; Miki, S. Synthesis2006, 4131.

Barbayianni, E.; Fotakopoulou, I.; Schmidt, M.; Constantinou-Kokotou, V.; Bornscheuer, U.T.; Kokotos, G. J. Org. Chem.2005, 70, 8730.

Other reactions useful for the hydrolysis of esters may be found in Section 30A (Protection of Carboxylic Acid Derivatives).

SECTION 24: ACID DERIVATIVES FROM ETHERS, EPOXIDES, AND THIOETHERS

Rowley, J.M.; Lobkovsky, E.B.; Coates, G.W. J. Am. Chem. Soc.2007, 129, 4948.

Svetlakov, N.V.; Nikitin, V.G.; Nikolaeva, E.A. Russ. J. Org. Chem.2007, 43, 771.

SECTION 25: ACID DERIVATIVES FROM HALIDES AND SULFONATES

Niu, D.-F.; Xiao, L.-P.; Zhang, A.-J.; Zhang, G.-R.; Tan, Q.-Y.; Lu, J.-X. Tetrahedron2008, 64, 10517.

Cacchi, S.; Cotet, C.L.; Fabrizi, G.; Forte, G.; Goggiamani, A.; Martín, L.; Martínez, S.; Molins, E.; Moreno-Mañas, M.; Petrucci, F.; Roig, A.; Vallribera, A. Tetrahedron2007, 63, 2519.

Zhao, X.; Alper, H.; Yu, Z. J. Org. Chem.2006, 71, 3988.

Berger, P.; Bessmernykh, A.; Caille, J.-C.; Mignonac, S. Synthesis2006, 3106.

Nadal, M.L.; Bosch, J.; Vila, J.M.; Klein, G.; Ricart, S.; Moretó, J.S. J. Am. Chem. Soc.2005, 127, 10476.

Jones, R.V.H.; Lindsell, W.E.; Palmer, D.D.; Preston, P.N.; Whitton, A.J. Tetrahedron Lett.2005, 46, 8695.

Mutule, I.; Suna, E. Tetrahedron2005, 61, 11168.

SECTION 26: ACID DERIVATIVES FROM HYDRIDES

Giri, R.; Yu, J.-Q. J. Am. Chem. Soc.2008, 130, 14082.

Crich, D.; Zou, Y. J. Org. Chem.2005, 70, 3309.

Ohashi, S.; Sakaguchi, S.; Ishii, Y. Chem. Commun.2005, 486.

SECTION 27: ACID DERIVATIVES FROM KETONES

Zhang, Y.; Jiao, J.; Flowers, II, R.A. J. Org. Chem.2006, 71, 4516.

SECTION 28: ACID DERIVATIVES FROM NITRILES

Mukherjee, C.; Zhu, D.; Biehl, E.R.; Parmar, R.R.; Hua, L. Tetrahedron2006, 62, 6150.

SECTION 29: ACID DERIVATIVES FROM ALKENES

Williams, C.M.; Johnson, J.B.; Rovis, T. J. Am. Chem. Soc.2008, 130, 14936.

Takaya, J.; Iwasawa, N. J. Am. Chem. Soc.2008, 130, 15254.

Tanaka, R.; Nakano, K.; Nozaki, K. J. Org. Chem.2007, 72, 8671.

SECTION 30: ACID DERIVATIVES FROM MISCELLANEOUS COMPOUNDS

Yeung, C.S.; Dong, V.M. J. Am. Chem. Soc.2008, 130, 7826.

Ochiai, H.; Jang, M.; Hirano, K.; Yorimitsu, H.; Oshima, K. Org. Lett.2008, 10, 2681.

Takaya, J.; Tadami, S.; Ukai, K.; Iwasawa, N. Org. Lett.2008, 10, 2697.

Khurana, J.M.; Sharma, P.; Gogia, A.; Kandpal, B.M. Org. Prep. Proceed. Int.2007, 39, 185.

Ukai, K.; Aoki, M.; Takaya, J.; Iwasawa, N. J. Am. Chem. Soc.2006, 128, 8706.

SECTION 30A: PROTECTION OF CARBOXYLIC ACID DERIVATIVES

NO ADDITIONAL EXAMPLES

Other reactions useful for the protection of carboxylic acids are included in Section 107 (Esters from Carboxylic Acid Derivatives) and Section 23 (Carboxylic Acid Derivatives from Esters).

Taksande, K.N.; Sakate, S.S.; Lokhande, P.D. Tetrahedron Lett.2006, 47, 643.

CHAPTER 3

PREPARATION OF ALCOHOLS

SECTION 31: ALCOHOLS AND THIOLS FROM ALKYNES

NO ADDITIONAL EXAMPLES

SECTION 32: ALCOHOLS AND THIOLS FROM ACID DERIVATIVES

Zhou, Y.; Gao, G.; Li, H.; Qu, J. Tetrahedron Lett.2008, 49, 3260.

Wei, Y.-J.; Ren, H.; Wang, J.-X. Tetrahedron Lett.2008, 49, 5697.

Ohta, T.; Kamiya, M.; Nobutomo, M.; Kusui, K.; Furukawa, I. Bull. Chem. Soc. Jpn.2005, 78, 1856.

SECTION 33: ALCOHOLS AND THIOLS FROM ALCOHOL AND THIOLS

Kim, I.S.; Ngai, M.-Y.; Krische, M.J. J. Am. Chem. Soc.2008, 130, 6340.

Fujita, K.-i.; Asai, C.; Yamaguchi, T.; Hanasaka, F.; Yamaguchi, R. Org. Lett.2005, 7, 4017.

SECTION 34: ALCOHOLS AND THIOLS FROM ALDEHYDES

The following reaction types are included in this section:

A. Reductions of Aldehydes to Alcohols

B. Alkylation of Aldehydes, Forming Alcohols

SECTION 34A: REDUCTIONS OF ALDEHYDES TO ALCOHOLS

Su, F.-Z.; He, L.; Ni, J.; Cao, Y.; He, H.-Y.; Fan, K.-N. Chem. Commun.2008, 3531.

Sambher, S.; Baskar, C.; Dhillon, R.S. Synth. Commun.2008, 38, 2150.

Xie, J.-H.; Zhou, Z.-T.; Kong, W.-L.; Zhou, Q.-L. J. Am. Chem. Soc.2007, 129, 1868.

Casey, C.P.; Guan, H. J. Am. Chem. Soc.2007, 129, 5816.

Shaikh, N.S.; Junge, K.; Beller, M. Org. Lett.2007, 9, 5429.

Heydari, A.; Khaksar, S.; Akbari, J.; Esfandyari, M.; Pourayoubi, M.; Tajbakhsh, M. Tetrahedron Lett.2007, 48, 1135.

Omote, M.; Tanaka, N.; Tarui, A.; Sato, K.; Kumadaki, I.; Ando, A. Tetrahedron Lett.2007, 48, 2989.

Wessjohann, L.A.; Schrekker, H.S. Tetrahedron Lett.2007, 48, 4323.

Li, X.; List, B. Chem. Commun.2007, 1739.

Giacomini, D.; Galletti, P.; Quintavalla, A.; Gucciardo, G.; Paradisi, F. Chem. Commun.2007, 4038.

Kidwai, M.; Bansal, V.; Saxena, A.; Shankar, R.; Mozumdar, S. Tetrahedron Lett.2006, 47, 4161.

Xing, Y.; Chen, J.-S.; Dong, Z.-R.; Li, Y.-Y.; Gao, J.-X. Tetrahedron Lett.2006, 47, 4501.

REVIEW

“Transition Metal-Catalyzed Hydrosilylation Of Carbonyl Compounds And Imines. A Review” Díez-González, S.; Nolan, S.P. Org. Prep. Proceed. Int.2007, 39, 523.

SECTION 34B: ALKYLATION OF ALDEHYDES, FORMING ALCOHOLS

ASYMMETRIC ALKYLATIONS

Kim, H.; MacMillan, D.W.C. J. Am. Chem. Soc.2008, 130, 398.

Boxer, M.B.; Akakura, M.; Yamamoto, H. J. Am. Chem. Soc.2008, 130, 1580.

Hajra, S.; Giri, A.K. J. Org. Chem.2008, 73, 3935.

Jin, M.-J.; Sarkar, S.M.; Lee, D.-H.; Qiu, H. Org. Lett.2008, 10, 1235.

Appelt, H.R.; Limberger, J.B.; Weber, M.; Rodrigues, O.E.D.; Oliveira, J.S.; Lüdtke, D.S.; Braga, A.L. Tetrahedron Lett.2008, 49, 4956.

Huang, X.; Wu, L.; Xu, J.; Zong, L.; Hu, H.; Cheng, Y. Tetrahedron Lett.2008, 49, 6823.

Burguete, M.I.; Escorihuela, J.; Luis, S.V.; Lledós, A.; Ujaque, G. Tetrahedron2008, 64, 9717.

Malkov, A.V.; Westwater, M.-M.; Gutnov, A.; Ramírez-López, P.; Friscourt, F.; Kadlčíková, A.; Hodačová, J.; Rankovic, Z.; Kotora, M.; Kočovský, P. Tetrahedron2008, 64, 11335.

Parrott II, R.W.; Dore, D.D.; Chandrashekar, S.P.; Bentley, J.T.; Morgan, B.S.; Hitchcock, S.R. Tetrahedron Asymmetry2008, 19, 607.

Cheng, Y.-Q.; Bian, Z.; Kang, C.-Q.; Guo, H.-Q.; Gao, L.-X. Tetrahedron Asymmetry2008, 19, 1572.

Grach, G.; Reboul, V.; Metzner, P. Tetrahedron Asymmetry200819, 1744.

Muramatsu, Y.; Harada, T. Angew. Chem. Int. Ed.2008, 47, 1088.

Tanaka, T.; Sano, Y.; Hayashi, M. Chemistry: Asian J.2008, 3, 1465.

Simonini, V.; Benaglia, M.; Pignataro, L.; Guizzetti, S.; Celentano, G. Synlett2008, 1061.

Hrdina, R.; Boyd, T.; Valterová, I.; Hodačová, J.; Kotora, M. Synlett2008, 3141.

Yamamoto, K.; Tsurumi, K.; Sakurai, F.; Kondo, K.; Aoyama, T. Synthesis2008, 3585.

Ukon, T.; Harada, T. Eur. J. Org. Chem.2008, 4405.

Hargaden, G.C.; O’Sullivan, T.P.; Guiry, P.J. Org. Biomol. Chem.2008, 6, 562.

Ramasastry, S.S.V.; Zhang, H.; Tanaka, F.; Barbas, III, C.F. J. Am. Chem. Soc.2007, 129, 288.

Yang, Y.; Zhu, S.-F.; Duan, H.-F.; Zhou, C.-Y.; Wang, L.-X.; Zhou, Q.-L. J. Am. Chem. Soc.2007, 129, 2248.

Lee, S.; MacMillan, D.W.C. J. Am. Chem. Soc.2007, 129, 15438.

Huang, Z.; Lai, H.; Qin, Y. J. Org. Chem.2007, 72, 1373.

Milburn, R.R.; Shakil Hussain, S.M.; Prien, O.; Ahmed, Z.; Snieckus, V. Org. Lett.2007, 9, 4403.

Sedelmeier, J.; Bolm, C. J. Org. Chem.2007, 72, 8859.

Cortez, N.A.; Aguirre, G.; Parra-Hake, M.; Somanathan, R. Tetrahedron Lett.2007, 48, 4335.

Takeuchi, K.; Takeda, T.; Fujimoto, T.; Yamamoto, I. Tetrahedron2007, 63, 5319.

Bisai, A.; Singh, P.K.; Singh, V.K. Tetrahedron2007, 63, 598.

Kelsen, V.; Pierrat, P.; Gros, P.C. Tetrahedron2007, 63, 10693.

Arai, T.; Endo, Y.; Yanagisawa, A. Tetrahedron Asymmetry2007, 18, 165.

Liu, L.-y.; Sun, J.; Liu, N.; Chang, W.-X.; Li, J. Tetrahedron Asymmetry2007, 18, 710.

Chai, Z.; Liu, X.-Y.; Zhang, J.-K.; Zhao, G. Tetrahedron Asymmetry2007, 18, 724.

Zhong, J.; Guo, H.; Wang, M.; Yin, M.; Wang, M. Tetrahedron Asymmetry2007, 18, 734.

Bulut, A.; Aslan, A.; Izgü, E.Ç.; Dogan, Ö. Tetrahedron Asymmetry2007, 18, 1013.

Harada, T.; Ukon, T. Tetrahedron Asymmetry2007, 18, 2499.

Xia, G.; Yamamoto, H. J. Am. Chem. Soc.2006, 128, 2554.

Sato, I.; Asakura, N.; Iwashita, T. Tetrahedron Asymmetry2007, 18, 2638.

Hargaden, G.C.; McManus, H.A.; Cozzi, P.G.; Guiry, P.J. Org. Biomol. Chem.2007, 5, 763.

Cozzi, P.G.; Kotrusz, P. J. Am. Chem. Soc.2006, 128, 4940.

Evans, D.A.; Aye, Y. J. Am. Chem. Soc.2006, 128, 11034.

Wu, K.-H.; Gau, H.-M. J. Am. Chem. Soc.2006, 128, 14808.

Kong, J.R.; Krische, M.J. J. Am. Chem. Soc.2006, 128, 16040.

Wu, P.-Y.; Wu, H.-L.; Uang, B.-J.