Sulfur-Containing Reagents E-Book

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Serie: Handbook of Reagents for Organic Synthesis
• Sprache: Englisch

Seitenzahl: 1862

Veröffentlichungsjahr: 2013

Beschreibung

There are a lot of books available about the chemistry and biology of sulfur. However, this is the first book with a compilation of all relevant Sulfur containing reagents. Synthetic chemists, most particularly in the medicinal and pharmaceutical chemists, are often called upon to prepare compounds that contain Sulfur as a key structural feature. In the past, this seemed to be a domain for specialists; today every synthetic chemist working in these area is expected to synthesize compounds containing sulfides, sulfates, sulfones, etc. This book offers an important source of information for the selection and handling of the right reagents.

Leseprobe

Contents

Cover

Other Titles in this Collection

Title Page

Copyright

Dedication

e-EROS Editorial Board

Preface

Introduction

Short Note on InChIs and InChIKeys

Organic Synthesis Procedures Featuring the Synthesis of Organosulfur Compounds and Preparative Applications thereof, Volumes 65–85

A: Allyl Triflone

Aminoiminomethanesulfonic Acid

p-Anisolesulfonyl Chloride1

Anthracenesulfonamide

B: 1-Benzenesulfinyl Piperidine

Benzenesulfonic Acid, 2-Nitro-, (1-Methylethylidene)hydrazide

Benzenesulfonic Anhydride

Benzenesulfonyl Bromide

Benzimidazolium Triflate

(1R,5R)-2H -1,5-Benzodithiepin-3(4H)-one 1,5-Dioxide

3H -1,2-Benzodithiol-3-one 1,1-Dioxide

Benzothianthrene Oxide

Benzothiazole-2-sulfonyl Chloride

4-Benzyloxazolidine-2-thione

3-(2-Benzyloxyacetyl)thiazolidine-2-thione1

Benzyltriethylammonium Tetrathiomolybdate

N -Benzyl Triflamide

4,4 ′ -Bis(2-amino-6-methylpyrimidyl) Disulfide

Bis(2,2 ′ -bipyridyl)silver(II) Peroxydisulfate

N,N′ -Bis(tert -butoxycarbonyl)-N′′ -trifluoromethanesulfonylguanidine

[N,N ′ -[1,2-Bis(3,5-dimethylphenyl)-1,2-ethanediyl]bis(1,1,1-trifluoromethanesulfonamidato)]-methylaluminum1

2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-Disulfide1

2,3-Bis[(4-methylphenyl)thio]-1,3,2,4-dithiadiphosphetane 2,4-Disulfide

2,4-Bis(methylthio)-1,3,2,4-dithiadiphosphetane 2,4-Disulfide

N -[Bis(methylthio)methylene]-p -toluenesulfonamide

Bis[N -(p -toluenesulfonyl)]selenodiimide

1-[Bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6-pentafluorobenzene1

Bis(4-trimethylsilylphenyl) Disulfide and Bis(4-trimethylsilylphenyl) Diselenide

Boron Trifluoride–Dimethyl Sulfide1

4-Bromobenzenesulfonyl Azide

4-Bromobenzenesulfonyl Chloride

(4R,5R)-2-Bromo-1,3-bis-(4-methylphenyl sulfonyl)-4,5-diphenyl-1,3,2-diazaborolidine and (4S,5S)-2-Bromo-1,3-bis-(4-methylphenyl sulfonyl)-4,5-diphenyl-1,3,2-diazaborolidine

Bromodifluorophenylsulfanylmethane

Bromomethanesulfonyl Phenyl Tetrazole1 (Chloro)

2-(2-Butenylthio)benzothiazole

tert-Butyl N -Lithio-N -(p -toluenesulfonyloxy)carbamate

2-[N-(tert -Butyloxycarbonyl)aminophenyl]ethanethiol

tert-Butylsulfonyl Chloride

tert-Butyltetrazolylthiol

C: 10-Camphorsulfonyl Chloride1

Carbomethoxysulfenyl Chloride

Carbon Disulfide1

Cerium(IV) Ammonium Sulfate1

Cesium Fluoroxysulfate

N-Chloro-N-cyclohexylbenzenesulfonamide1

Chloromethyl p-Tolyl Sulfide1

Chloromethyl p-Tolyl Sulfone

4-Chlorophenyl Chlorothionoformate

4-(4-Chlorophenyl)-3-hydroxy-2(3H)thiazolethione

N-Chlorosuccinimide–Dimethyl Sulfide1

Chloro(thexyl)borane–Dimethyl Sulfide

Copper(II) Sulfate

Copper, (2-Thiophenecarboxylato-κO2, κS1)

Copper(II) Toluenesulfonate

Copper(I) Trifluoromethanesulfonate

Copper(II) Trifluoromethanesulfonate

D: Dibromoborane–Dimethyl Sulfide1

Dibutyl(trifluoromethanesulfoxy)stannane

Dicarbonyl(cyclopentadienyl)[(dimethylsulfonium)methyl]iron Tetrafluoroborate1

Dichloroborane–Dimethyl Sulfide1

2-2-Difluorovinyl p-Toluenesulfonate

2,5-Dihydro-2,2-dimethyl-5,5-bis(propylthio)-1,3,4-oxadiazole

2,3-Dihydro-2-phenylimidazo[2,1-b]benzothiazole

Diisopropyl Methylsulfanyldifluoromethylphosphonate

4-(Dimethylamino)pyridinium Chlorosulfite Chloride

Dimethyl Bis(methylthio)methylphosphonate1

6,6-Dimethyl-1,4-diseleno-3,7-tetrasulfide

N,N-Dimethyldithiocarbamoylacetonitrile1

N-(1,1-Dimethylethyl)benzenesulfenamide

N,N-Dimethyl-O-(methylsulfonyl)-hydroxylamine1

Dimethyl(methylthio)sulfonium Tetrafluoroborate1

Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate

cis-3-[N-(3,5-Dimethylphenyl)benzenesulfonamido]borneol1

Dimethylsuccinimidosulfonium Tetrafluoroborate

Dimethyl Sulfoxide–Iodine

Dimethyl Sulfoxide–Methanesulfonic Anhydride1

Dimethyl Sulfoxide–Phosphorus Pentoxide1

Dimethyl Sulfoxide–Silver Tetrafluoroborate

Dimethyl Sulfoxide–Sulfur Trioxide/Pyridine1

S,S-Dimethyl-N-(p -toluenesulfonyl)sulfilimine1,2

S,S-Dimethyl-N-(p -toluenesulfonyl)sulfoximine1

2,4-Dinitrobenzenesulfonyl Chloride

3,5-Dinitrobenzenesulfonyl Chloride

2,4-Dinitrobenzenesulfonylhydrazide

2-(1,3-Dioxan-2-yl)ethylsulfonyl Chloride

1,1-Dioxobenzo[b]-thiophene-2-yl Methyloxycarbonyl Chloride

Diphenylbis(1,1,1,3,3,3-hexafluoro-2-phenyl-2-propoxy)sulfurane1

(R,R)-1,2-Diphenyl-1,2-diaminoethane N,N′-Bis[3,5-bis(trifluoromethyl)benzenesulfonamide]

N-(Diphenylmethylene)benzenesulfonamide and N -(Diphenylmethylene)-4-methylbenzenesulfonamide

Diphenyl Sulfoxide

2,2′-Dipyridyl Disulfide-N,N′ -dioxide

1,2,4-Dithiazolidine-3,5-dione

1,3-Dithienium Tetrafluoroborate

trans-1,3-Dithiolane 1,3-Dioxide1

1,4-Dithiothreitol1

tert-Dodecanethiol

p -Dodecylbenzenesulfonyl Azide

E: Ethyl (Dimethylsulfuranylidene)acetate

S-Ethyl Ethanethiosulfinate

4-Ethylhexahydro-4-methyl-(4S,9aS)-pyrrolo[1,2-d][1,4]thiazepin-5(4H)-one

5-Ethylthio-1H-tetrazole

F: 2-Fluoro-3,3-dimethyl-2,3-dihydro-1,2-benzisothiazole 1,1-Dioxide

N-Fluoro-N-(phenylsulfonyl)benzenesulfonamide

Fluorosulfuric Acid

Fluorosulfuric Acid–Antimony(V) Fluoride1

G: Glyoxylyl Chloride p-Toluenesulfonylhydrazone1

H: 2-Hydroxyethyl Phenyl Sulfone

[Hydroxy(tosyloxy)iodo]benzene

I: Isopropyldiphenylsulfonium Tetrafluoroborate1

(S)-4-Isopropylthiazolidine-2-thione

L: (1R,2S)-1-Lithio-1-phenylsulfonyl-2-[(tert -butyldiphenyl)silyl]oxymethyl-oxirane

2-Lithio-N-phenylsulfonylindole

Lithium Butyl(phenylthio)cuprate1

Lithium Cyclopropyl(phenylthio)cuprate1

Lithium (3,3-Diethoxy-1-propen-2-yl)(phenylthio)cuprate1

Lithium 2-Lithiobenzenethiolate

Lithium 1-Methyl-2-(2-methyl-1-(E)-propenyl)cyclopropyl(phenylthio)cuprate

Lithium Phenylthio(trimethylstannyl)cuprate

Lithium Phenylthio(2-vinylcyclopropyl)cuprate1

M: (−)-(1R,2S,5R)-Menthyl (S)-p -Toluenesulfinate

6-Mercapto-4-dibenzofuranol

1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT)

Mesitylsulfonyl-1H -1,2,4-triazole

(R,R)-1,2-(Methanesulfonamido)-cyclohexane

Methanesulfonic Anhydride

Methanesulfonyl Chloride–Dimethylaminopyridine

Methoxycarbonylmethanesulfonyl Chloride

Methoxycarbonylsulfamoyl Chloride1

4-Methoxycarbonylthiolan-3-one

2-(2-Methoxyethoxy)-ethyl 2-(Chlorosulfonyl)-benzoate

Methoxyphenyl Benzenethiosulfinate

1-(4-Methoxyphenyl)-2-(4′-methylbenzylthio)ethylamine1

7-Methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone

Methoxy(phenylthio)methane1

Methoxy(phenylthio)trimethylsilylmethane

2-Methylallyl Phenyl Sulfone

2-Methylbenzothiazole1

Methylbis(methylthio)sulfonium Hexachloroantimonate1

Methyl α -Chloro- α-phenylthioacetate

Methyl Diethylamidosulfite1

Methyl Methanethiosulfonate1

4-Methyl-N-phenylbenzene Sulfonimidoyl Chloride

1-Methyl-2(1H)-pyridinethione

Methylsulfenyl Trifluoromethanesulfonate

(+)-(S)-N-Methylsulfonylphenylalanyl Chloride

2-Methylsulfonyl-3-phenyl-1-prop-2-enyl Chloroformate

Methyl Thioglycolate

Methylthiomaleic Anhydride

1-(Methylthiomethyl)benzotriazole

Methylthiomethyl p -Tolyl Sulfone1

(E)-3-Methylthio-2-propenyl p-Tolyl Sulfone1

2-(Methylthio)tetrahydrofuran

5-Methylthio-1H-tetrazole

Methyl N-(p-Toluenesulfonyl)carbamate

α-Methyltoluene-2, α-sultam1

Methyl p-Toluenethiosulfonate1

N-Methyltrifluoromethanesulfonamide

Methyltrifluoromethanesulfonate

(–)-2-exo-Morpholinoisobornane-10-thiol

N: o-Nitrobenzenesulfonyl Azide

o-Nitrobenzenesulfonyl Chloride

o-Nitrobenzenesulfonylhydrazide

p-Nitrobenzenesulfonyl-4-nitroimidazole

p-Nitrobenzenesulfonyloxyurethane1

5-Nitro-3H-1,2-benzoxathiole S,S-Dioxide

Nitrosylsulfuric Acid

1,1,1,2,2,3,3,4,4-Nonafluoro-6-(methane-sulfinyl)hexane

O: Oxodimethoxyphosphoranesulfenyl Chloride1

P: Pentafluorosulfanyl Chloride

1H,1H,2H,2H-Perfluorodecanethiol

Peroxydisulfuryl Difluoride1

Phenyl Chlorothionocarbonate

1-Phenyl-2-(phenylsulfanyl)ethyl Acetate

4-Phenylsulfonyl-2-butanone Ethylene Acetal

N -(Phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine1

(2-Phenylsulfonyl)ethoxy Dichlorophosphine

α-Phenylsulfonylethyllithium

(2-Phenylsulfonylethyl)trimethylsilane

Phenylsulfonylfluoromethylphosphonate

(1S,6S)-2-(Phenylsulfonyl)-7-oxabicyclo-[4.1.0]hept-2-ene

(E,E)-N-Phenylsulfonyl-4-phenyl-1-aza-1,3-butadiene1

3-(Phenylsulfonyl)propanal Ethylene Acetal

1-Phenylsulfonyl-1H-tetrazole

(E)-1-Phenylsulfonyl-2-trimethylsilylethylene1

1-Phenyl-2-tetrazoline-5-thione

2-Phenylthioethanol

(Phenylthio)nitromethane1

N-Phenylthiophthalimide1

1-Phenylthiovinyl Triphenylphosphonium Iodide

Se-Phenyl p-Tolueneselenosulfonate1

N-Phenyltrifluoromethanesulfonimide1

Phthalimidosulfenyl Chloride1

Potassium t ert-Butoxide–Dimethyl Sulfoxide1

Potassium Hydroxide–Dimethyl Sulfoxide

Potassium Monoperoxysulfate

Potassium o-Nitrobenzeneperoxysulfonate

Potassium Nitrosodisulfonate1

1,3-Propanedithiol Bis(p-toluenesulfonate)1

N-Propenoyl Camphor-10,2-sultam1

3-Propionylthiazolidine-2-thione1

2-Pyridinesulfonyl Chloride

N-(2-Pyridyl)bis(trifluoromethanesulfonimide)

S: Sodium Dodecyl Sulfate

N -Sulfinyl-p -toluenesulfonamide1

9-(2-Sulfo)fluorenylmethoxycarbonyl Chloride

Sulfonic Acid, Polymer-supported

o -Sulfoperbenzoic Acid

Sulfur Trioxide1

T: N, N, N′, N′-Tetrabromobenzene-1,3-disulfonamide (TBBDS)

Tetrachlorothiophene Dioxide

2,2,4,4-Tetramethylcyclobutan-1-one-3-thione

1,1′-(Thiocarbonyl)bis(1H -benzotriazole)

2-Thiono-1,3-dioxol-4-ene

Thiophenol–Azobisisobutyronitrile

Thiophenol, Polymer-supported

Thiophosphoryl Chloride

2-Thiopyridyl Chloroformate1

Thiourea Dioxide1

p -Toluenesulfinic Acid

p-Toluenesulfonyl Bromide

p -Toluenesulfonyl Chloride and Related Reagents, Polymer-supported

O-p-Toluenesulfonylhydroxylamine

[N -(p -Toluenesulfonyl)imino]phenyliodinane

p-Toluenesulfonylmethylene Triphenylphosphorane

(R)-(+)-p -Tolylsulfinylacetic Acid

(R)-(+)-α-(p -Tolylsulfinyl)-N,N-dimethylacetamide

(R)-(+)-3-(p -Tolylsulfinyl)propionic Acid

Tosyl Azide, Polymer-supported

β-Tosylethylamine

β-Tosylethylazide

6-Tosyl-3-oxa-6-azabicyclo[3.1.0]hexane

Tri(tert-butoxy)silanethiol

Tricarbonyl[(2,3,4,5,6,7-η)-thiepin-1,1-dioxide]chromium(0)1

2,2,2-Trichloroethoxysulfonamide

2,2,2-Trichloroethyl-N-tosyloxycarbamate

Triethylsilyl Trifluoromethanesulfonate1

Trifluoromethanesulfonic Acid1

Trifluoromethanesulfonic Anhydride

Trifluoromethanesulfonyl Azide

Trifluoromethanesulfonyl Chloride1

Trifluoromethanesulfonylmethyl Methyl Sulfone

S-(Trifluoromethyl)dibenzothiophenium Triflate1

Trifluoromethyl Phenyl Sulfone

{[(Trifluoromethyl)sulfonyl]ethynyl}-benzene1

(S)-N -Trifluoromethylsulfonyl-2-isopropylaziridine

[1,1,1-Trifluoro-N -[(trifluoromethyl)sulfonyl]methanesulfonamidato-κN](triphenylphosphine)

1,1,1-Trifluoro-N-[(trifluoromethyl)sulfonyl]-N-(trimethylsilyl)methanesulfonamide

2,4,6-Triisopropylbenzenesulfonyl Azide1

2,4,6-Triisopropylbenzenesulfonyl Hydrazide1

Triisopropylbenzenesulfonyl Tetrazole

Triisopropylsilylethynyl Triflone

Triisopropylsilyl Trifluoromethanesulfonate1

2-Trimethylsilyl-1,3-benzothiazole

[N -(2-(Trimethylsilyl)ethanesulfonyl)imino]phenyliodane

(Trimethylsilyl)methanesulfonyl Chloride–Cesium Fluoride

2-(Trimethylsilyl)phenyl Triflate

Triphenylphosphonium 3,3-Dimethyl-1,2,5-thiadiazolidine 1,1-Dioxide

Triphenyl Thioborate

Trityl Thionitrite

List of Contributors

Reagent Formula Index

Subject Index

General Abbreviations

Other Titles in this Collection

Reagents for Radical and Radical Ion Chemistry

Edited by David Crich

ISBN 978 0 470 06536 5

Catalyst Components for Coupling Reactions

Edited by Gary A. Molander

ISBN 978 0 470 51811 3

Fluorine-Containing Reagents

Edited by Leo A. Paquette

ISBN 978 0 470 02177 4

Reagents for Direct Functionalization of C–H Bonds

Edited by Philip L. Fuchs

ISBN 0 470 01022 3

Reagents for Glycoside, Nucleotide, and Peptide Synthesis

Edited by David Crich

ISBN 0 470 02304 X

Reagents for High-Throughput Solid-Phase and Solution-Phase Organic Synthesis

Edited by Peter Wipf

ISBN 0 470 86298 X

Chiral Reagents for Asymmetric Synthesis

Edited by Leo A. Paquette

ISBN 0 470 85625 4

Activating Agents and Protecting Groups

Edited by Anthony J. Pearson and William R. Roush

ISBN 0 471 97927 9

Acidic and Basic Reagents

Edited by Hans J. Reich and James H. Rigby

ISBN 0 471 97925 2

Oxidizing and Reducing Agents

Edited by Steven D. Burke and Rick L. Danheiser

ISBN 0 471 97926 0

Reagents, Auxiliaries, and Catalysts for C–C Bond Formation

Edited by Robert M. Coates and Scott E. Denmark

ISBN 0 471 97924 4

e-EROS

For access to information on all the reagents covered in the Handbooks of Reagents for Organic Synthesis, and many more, subscribe to e-EROS on the Wiley Interscience website. A database is available with over 200 new entries and updates every year. It is fully searchable by structure, substructure and reaction type and allows sophisticated full text searches. http://www.mrw.interscience.wiley.com/eros/

This edition first published 2009

2009 John Wiley & Sons Ltd

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Library of Congress Cataloging-in-Publication Data

Handbook of reagents for organic synthesis.

p.cm

Includes bibliographical references.

Contents: [1] Reagents, auxiliaries and catalysts for C–C bond formation / edited by Robert M. Coates and Scott E. Denmark [2] Oxidizing and reducing agents / edited by Steven D. Burke and Riek L. Danheiser [3] Acidic and basic reagents / edited by Hans J. Reich and James H. Rigby [4] Activating agents and protecting groups / edited by Anthony J. Pearson and William R. Roush [5] Chiral reagents for asymmetric synthesis / edited by Leo A. Paquette [6] Reagents for high-throughput solid-phase and solution-phase organic synthesis / edited by Peter Wipf [7] Reagents for glycoside, nucleotide and peptide synthesis / edited by David Crich [8] Reagents for direct functionalization of C–H bonds/edited by Philip L. Fuchs [9] Fluorine-Containing Reagents/edited by Leo A. Paquette [10] Catalyst Components for Coupling Reactions / edited by Gary A. Molander [11] Reagents for Radical and Radical Ion Chemistry/edited by David Crich [12] Sulfur-Containing Reagents / edited by Leo A. Paquette

ISBN 0-471-97924-4 (v. 1)ISBN 0-471-97926-0 (v. 2)ISBN 0-471-97925-2 (v. 3)ISBN 0-471-97927-9 (v. 4)ISBN 0-470-85625-4 (v. 5)ISBN 0-470-86298-X (v. 6)ISBN 0-470-02304-X (v. 7)ISBN 0-470-01022-3 (v. 8)ISBN 978-0-470-02177-4 (v. 9)ISBN 978-0-470-51811-3 (v.10)ISBN 978-0-470-06536-5 (v. 11)ISBN 978-0-470-74872-5 (v.12)1. Chemical tests and reagents.2. Organic compounds-Synthesis.QD77.H37 199998-53088547'.2 dc 21CIP

A catalogue record for this book is available from the British Library.

ISBN 13: 978-0-470-74872-5

This volume is dedicated to Dr. Gerald Berkelhammer who introduced me to the field of organosulfur chemistry during summer employment (1957) as a fledgling graduate student while working at the American Cyanamid Company in Stamford, Connecticut.

e-EROS Editorial Board

Editor-in-Chief

David Crich

Institut de Chimie des Substances Naturelles (ICSN),

Gif-sur-Yvette, France

Executive Editors

André B. Charette

Université de Montréal, Montréal, QC, Canada

Philip L. Fuchs

Purdue University, West Lafayette, IN, USA

Gary A. Molander

University of Pennsylvania, Philadelphia, PA, USA

Founding Editor

Leo A. Paquette

The Ohio State University, Columbus, OH, USA

Preface

The eight-volume Encyclopedia of Reagents for Organic Synthesis (EROS), authored and edited by experts in the field, and published in 1995, had the goal of providing an authoritative multivolume reference work describing the properties and reactions of approximately 3000 reagents. With the coming of the Internet age and the continued introduction of new reagents to the field as well as new uses for old reagents, the electronic sequel, e-EROS, was introduced in 2002 and now contains in excess of 4000 reagents, catalysts, and building blocks making it an extremely valuable reference work. At the request of the community, the second edition of the encyclopedia, EROS II, was published in March 2009 and contains the entire collection of reagents at the time of publication in a 14 volume set.

Although the comprehensive nature of EROS and EROS II and the continually expanding e-EROS render them invaluable as reference works, their very size limits their practicability in a laboratory environment. For this reason, a series of inexpensive one-volume Handbooks of Reagents for Organic Synthesis (HROS), each focused on a specific subset of reagents, was introduced by the original editors of EROS in 1999:

Reagents, Auxiliaries, and Catalysts for C–C Bond FormationEdited by Robert M. Coates and Scott E. Denmark

Oxidizing and Reducing AgentsEdited by Steven D. Burke and Rick L. Danheiser

Acidic and Basic ReagentsEdited by Hans J. Reich and James H. Rigby

Activating Agents and Protecting GroupsEdited by Anthony J. Pearson and William R. Roush

This series has continued over the past several years with the publication of another series of HROS volumes, each edited by a current or past member of the e-EROS editorial board:

Chiral Reagents for Asymmetric SynthesisEdited by Leo A. Paquette

Reagents for High-Throughput Solid-Phase and Solution-Phase Organic SynthesisEdited by Peter Wipf

Reagents for Glycoside, Nucleotide, and Peptide SynthesisEdited by David Crich

Reagents for Direct Functionalization of C–H BondsEdited by Philip L. Fuchs

Fluorine-Containing ReagentsEdited by Leo A. Paquette

Catalyst Components for Coupling ReactionsEdited by Gary A. Molander

Reagents for Radical and Radical Ion ChemistryEdited by David Crich

This series now continues with this volume entitled Sulfur-Containing Reagents, edited by Leo Paquette, the originator and longtime guiding light of the EROS and HROS volumes, in addition to the online version, e-EROS. This 12th volume in the HROS series, like its predecessors, is intended to be an affordable, practicable compilation of reagents arranged around a central theme that it is hoped will be found at arm's reach from synthetic chemists worldwide. The reagents have been selected to give broad relevance to the volume, within the limits defined by the subject matter of organosulfur reagents. We have enjoyed putting this volume together and hope that our colleagues will find it as much enjoyable and useful to read and consult.

David CrichCentre de Recherche de Gif-sur-YvetteInstitut de Chimie des Substances NaturellesGif-sur-Yvette, France

Introduction

The widespread use of sulfur-containing reagents by synthetic chemists is a reflection of the diversity of properties offered by this broad class of compounds. The enormous divergence in the reactivity of divalent and tetravalent sulfur reagents, the stereochemical issues offered by sulfoxides, and the ionizability of sulfonic acids represent only a few of the many facets of this collective group of reagents. The resulting demands placed on chemists for the appropriate adaptation of a given reagent emerge in many forms, not the least of which bear on one's knowledge of reactivity, availability of building blocks, appreciation of the consequences of associated changes in electronic character, and the like. As a consequence of many recent developments, it was deemed appropriate to incorporate into a single volume a compilation that brings together a large fraction of the more useful organosulfur reagents as well as key sulfur-containing promoters that are currently in vogue. As usual, the compilation has been arranged alphabetically in order to facilitate searching. An added benefit is to foster the scanning for information since proximal arrangements by compound type are not prevalent.

The selection covered in this volume is built on the many important discoveries at the hands of numerous practitioners of our science. These achievements have been realized in conjunction with a very extensive physical organic base.

The featured reagents have been culled from three sources. A minority of the entries appeared initially in the Encyclopedia of Reagents for Organic Synthesis (EROS), which was published in 1995. Since that time, a significant number of entries involving these classical reagents have been updated (e-EROS), and this important add-on information is also found herein in the form of extensions to the original articles. The third pool of reagents is constituted of entirely new entries that detail the chemical and physical properties of an added subset of sulfur-containing compounds. In some instances, groups of reagents coincidentally appear in close proximity, thereby facilitating comparative analysis. Subsets consisting of meta-and para-nitrobenzenesulfonyl peroxide and of β-tosylethyl amine, hydrazine, and hydroxylamine are exemplary.

Among the opening segments of this volume is a section that illustrates those procedures relevant to the field that have appeared in volumes 65–85 of Organic Syntheses. It is hoped that these tried and tested protocols will provide a useful level of added guidance in selecting what course of action one might pursue. All in all, it is hoped that this handbook will prove to be a valued adjunct to researchers experienced in sulfur chemistry, and a particularly useful compilation for others seeking to gain a foothold in the field as expediently as possible. These goals will have been realized if advances materialize from exposure to its contents.

Leo A. PaquetteDepartment of ChemistryThe Ohio State UniversityColumbus, OH, USA

Short Note on InChIs and InChIKeys

The IUPAC International Chemical Identifier (InChITM) and its compressed form, the InChiKey, are strings of letters representing organic chemical structures that allow for structure searching with a wide range of online search engines and databases such as Google and PubChem. While they are obviously an important development for online reference works, such as Encyclopedia of Reagents for Organic Reactions (e-EROS), readers of this volume may be surprised to find printed InChi and InChIKey information for each of the reagents.

We introduced InChi and InChIKey to e-EROS in autumn 2009, including the strings in all HTML and PDF files. While we wanted to make sure that all users of e-EROS, the second print edition of EROS and all derivative Handbooks would find the same information, we appreciate that the strings will be of little use to the readers of the print editions, unless they treat them simply as reminders that e-EROS now offers the convenience of InChIs and InChIKeys, allowing the online users to make best use of their browsers and perform searches in a wide range of media.

If you would like to know more about InChIs and InChIKeys, please go to the e-EROS website: www.mrw.interscience.wiley.com/eros/ and click on the InChI and InChiKey link.

Organic Synthesis Procedures Featuring the Synthesis of Organosulfur Compounds and Preparative Applications thereof, Volumes 65–85

Synthesis of Organosulfur Compounds

N-(4-Acetamidophenylsulfonyl)-2-phenylacetamide

S. H. Chol, S. J. Hwang, and S. Chang; Org. Synth.2008, 85, 131.

2-(4′ -Acetylphenyl)thiophene

L. S. Liebeskind and E. Peña-Cabrera; Org. Synth.2000, 77, 135.

1-(Benzenesulfonyl)cyclopentane

H. S. Lin, M. J. Coghlan, and L. A. Paquette; Org. Synth.1989, 67, 157.

2-(N-Benzyl-N-mesitylenesulfonyl)amino-1-phenyl-1-propyl Propionate

A. Abiko; Org. Synth.2003, 19, 109.

(−)-(E,S)-3-(Benzyloxy)-1-butenyl Phenyl Sulfone

D. Enders, S. Von Berg, and B. Jandeleit; Org. Synth.2002, 78, 177.

2,2′ -Bi-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]dithiinylidene (BEDT-TTF)

J. Larsen and C. Lenoir; Org. Synth.1995, 72, 265.

n-Butyl 4-Chlorophenyl Sulfide

J. C. McWilliams, F. Fleitz, N. Zheng, and J. D. Armstrong III; Org. Synth.2003, 79, 43.

(−)-D-2, 10-Camphorsultam

M. C. Weismiller, J. C. Towson, and F. A. Davis; Org. Synth.1990, 69, 154.

(+)-(2R,8aS)-10-(Camphorylsulfonyl)oxaziridine

J. C. Towson, M. C. Weismiller, G. S. Lal, A. C. Sheppard, and F. A. Davis; Org. Synth.1990, 69, 158.

2-Chlorophenyl Phosphorodichloridothioate

V. T. Ravikumar and B. Ross; Org. Synth.1999, 76, 271.

4-(3-Cyclohexenyl)-2-phenylthio-1-butene

T. Ishiyama, N. Miyaura, and A. Suzuki; Org. Synth.1993, 71, 89.

4,5-Dibenzoyl-1,3-dithiole-1-thione

T. K. Hansen, J. Becher, T. Jrgensen, K. S. Varma, R. Khedekar, and M. P. Cava; Org. Synth.1976, 73, 270.

Dicyclohexylboron Trifluoromethanesulfonate

A. Abiko; Org. Synth.2003, 78, 103.

Diethyl [(Phenylsulfonyl)methyl]phosphonate

D. Enders, S. von Berg, and B. Jandeleit; Org. Synth.2002, 78, 169.

(+)-(2R,8aR*)-[(8,8-Dimethoxycamphoryl)sulfonyl]oxa-ziridine and (+)-(2R,8aR*)-[(8,8-Dichlorocamphoryl)-sulfonyl]oxaziridine

B.-C. Chen, C. K. Murphy, A. Kumar, R. T. Reddy, C. Clark, P. Zhou, B. M. Lewis, D. Gala, I. Mergelsberg, D. Scherer, J. Buckley, D. DiBenedetto, and F. A. Davis; Org. Synth.1995, 93, 159.

1S-(−)-1,3-Dithiane 1-Oxide

P. C. Bulman Page, J. P. Heer, D. Bethell, E. W. Collington, and D. M. Andrews; Org. Synth.1999, 76, 37.

Dithieno[3,2-b:2′,3′ -d]thiophene

J. Frev, S. Proemmel, M. A. Armitage, and A. B. Holmes; Org. Synth.2006, 83, 209.

Ethynyl p-Tolyl Sulfone

L. Waykole and L. A. Paquette; Org. Synth.1989, 67, 149.

Fluoromethyl Phenyl Sulfone

J. R. McCarthy, D. P. Matthews, and J. P. Paolini; Org. Synth.1995, 72, 209.

N-Hydroxy-4-(p-chlorophenyl)thiazole-2(3)-thione