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Beschreibung

Science of Synthesis provides a critical review of the synthetic methodology developed from the early 1800s to date for the entire field of organic and organometallic chemistry.

As the only resource providing full-text descriptions of organic transformations and synthetic methods as well as experimental procedures, Science of Synthesis is therefore a unique chemical information tool. Over 1000 world-renowned experts have chosen the most important molecular transformations for a class of organic compounds and elaborated on their scope and limitations.

The systematic, logical and consistent organization of the synthetic methods for each functional group enables users to quickly find out which methods are useful for a particular synthesis and which are not. Effective and practical experimental procedures can be implemented quickly and easily in the lab.// The content of this e-book was originally published in December 2007.

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Science of Synthesis

Science of Synthesis is the authoritative and comprehensive reference work for the entire field of organic and organometallic synthesis.

Science of Synthesis presents the important synthetic methods for all classes of compounds and includes:

Methods critically evaluated by leading scientists

Background information and detailed experimental procedures

Schemes and tables which illustrate the reaction scope

List of All Volumes

Science of Synthesis, Houben-Weyl Methods of Molecular Transformations

Category 1: Organometallics

1 Compounds with Transition Metal—Carbon π-Bonds and Compounds of Groups 10–8 (Ni, Pd, Pt, Co, Rh, Ir, Fe, Ru, Os)

2 Compounds of Groups 7–3 (Mn ···, Cr ···, V ···, Ti ···, Sc ···, La ···, Ac ···)

3 Compounds of Groups 12 and 11 (Zn, Cd, Hg, Cu, Ag, Au)

4 Compounds of Group 15 (As, Sb, Bi) and Silicon Compounds

5 Compounds of Group 14 (Ge, Sn, Pb)

6 Boron Compounds

7 Compounds of Groups 13 and 2 (Al, Ga, In, Tl, Be ··· Ba)

8 Compounds of Group 1 (Li ··· Cs)

Category 2: Hetarenes and Related Ring Systems

9 Fully Unsaturated Small-Ring Heterocycles and Monocyclic Five-Membered Hetarenes with One Heteroatom

10 Fused Five-Membered Hetarenes with One Heteroatom

11 Five-Membered Hetarenes with One Chalcogen and One Additional Heteroatom

12 Five-Membered Hetarenes with Two Nitrogen or Phosphorus Atoms

13 Five-Membered Hetarenes with Three or More Heteroatoms

14 Six-Membered Hetarenes with One Chalcogen

15 Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom

16 Six-Membered Hetarenes with Two Identical Heteroatoms

17 Six-Membered Hetarenes with Two Unlike or More than Two Heteroatoms and Fully Unsaturated Larger-Ring Heterocycles

Category 3: Compounds with Four and Three Carbon—Heteroatom Bonds

18 Four Carbon—Heteroatom Bonds: X—C≡X, X=C=X, X2C=X, CX4

19 Three Carbon—Heteroatom Bonds: Nitriles, Isocyanides, and Derivatives

21 Three Carbon—Heteroatom Bonds: Amides and Derivatives; Polyamides and Peptides; Lactams

22 Three Carbon—Heteroatom Bonds: Thio-, Seleno-, and Tellurocarboxylic Acids and Derivatives; Imidic Acids and Derivatives; Ortho Acid Derivatives

23 Three Carbon—Heteroatom Bonds: Ketenes and Derivatives

24 Three Carbon—Heteroatom Bonds: Ketene Acetals and Yne—X Compounds

Category 4: Compounds with Two Carbon-Heteroatom Bonds

25 Aldehydes

26 Ketones

27 Heteroatom Analogues of Aldehydes and Ketones

28 Quinones and Heteroatom Analogues

29 Acetals: Hal/X and O/O, S, Se, Te

30 Acetals: O/N, S/S, S/N, and N/N and Higher Heteroatom Analogues

31a Arene-X (X= Hal, O, S, Se, Te)

31b Arene-X (X= N, P)

Category 5: Compounds with One Saturated Carbon-Heteroatom Bond

34 Fluorine

35 Chlorine, Bromine, and Iodine

37 Ethers

39 Sulfur, Selenium, and Tellurium

40 Amines, Ammonium Salts, Haloamines, Hydroxylamines, Hydrazines, Triazanes, and Tetrazanes

41 Nitro, Nitroso, Azo, Azoxy, and Diazonium Compounds, Azides, Triazenes, and Tetrazenes

42 Organophosphorus Compounds (incl. RO-P and RN-P)

Category 6: Compounds with All-Carbon Functions

43 Polyynes, Arynes, Enynes, and Alkynes

44 Cumulenes and Allenes

45 Arenes, Quasiarenes, Annulenes, and Polyenes

46 1,3-Dienes

47 Alkenes

48 Alkanes

Preface

As our understanding of the natural world increases, we begin to understand complex phenomena at molecular levels. This level of understanding allows for the design of molecular entities for functions ranging from material science to biology. Such design requires synthesis and, as the structures increase in complexity as a necessity for specificity, puts increasing demands on the level of sophistication of the synthetic methods. Such needs stimulate the improvement of existing methods and, more importantly, the development of new methods. As scientists confront the synthetic problems posed by the molecular targets, they require access to a source of reliable synthetic information. Thus, the need for a new, comprehensive, and critical treatment of synthetic chemistry has become apparent. To meet this challenge, an entirely new edition of the esteemed reference work Houben–Weyl Methods of Organic Chemistry will be published starting in the year 2000.

To reflect the new broader need and focus, this new edition has a new title, Science of Synthesis, Houben–Weyl Methods of Molecular Transformations. Science of Synthesis will benefit from more than 90 years of experience and will continue the tradition of excellence in publishing synthetic chemistry reference works. Science of Synthesis will be a balanced and critical reference work produced by the collaborative efforts of chemists, from both industry and academia, selected by the editorial board. All published results from journals, books, and patent literature from the early 1800s until the year of publication will be considered by our authors, who are among the leading experts in their field. The 48 volumes of Science of Synthesis will provide chemists with the most reliable methods to solve their synthesis problems. Science of Synthesis will be updated periodically and will become a prime source of information for chemists in the 21st century.

Science of Synthesis will be organized in a logical hierarchical system based on the target molecule to be synthesized. The critical coverage of methods will be supported by information intended to help the user choose the most suitable method for their application, thus providing a strong foundation from which to develop a successful synthetic route. Within each category of product, illuminating background information such as history, nomenclature, structure, stability, reactivity, properties, safety, and environmental aspects will be discussed along with a detailed selection of reliable methods. Each method and variation will be accompanied by reaction schemes, tables of examples, experimental procedures, and a background discussion of the scope and limitations of the reaction described.

The policy of the editorial board is to make Science of Synthesis the ultimate tool for the synthetic chemist in the 21st century.

We would like to thank all of our authors for submitting contributions of such outstanding quality, and, also for the dedication and commitment they have shown throughout the entire editorial process.

October 2000

The Editorial Board

D. Bellus (Basel, Switzerland)

E. N. Jacobsen (Cambridge, USA)

S. V. Ley (Cambridge, UK)

R. Noyori (Nagoya, Japan)

M. Regitz (Kaiserslautern, Germany)

P. J. Reider (New Jersey, USA)

E. Schaumann (Clausthal-Zellerfeld, Germany)

I. Shinkai (Tsukuba, Japan)

E. J. Thomas (Manchester, UK)

B. M. Trost (Stanford, USA)

Category 2 (Hetarenes and Related Ring Systems): Cumulative Index

Preface

Product Class Overview

Structure Index

Name Reaction Index

Keyword Index

Author Index

Erratum

Abbreviations

Volume 9: Fully Unsaturated Small-Ring Heterocycles and Monocyclic Five-Membered Hetarenes with One Heteroatom

Introduction

G. Maas

9.1 Product Class 1: Oxirenes

K.-P. Zeller

9.2 Product Class 2: Thiirenes and Their Derivatives

N. Tokitoh and W. Ando

9.3 Product Class 3: Selenirenes

N. Tokitoh and W. Ando

9.4 Product Class 4: Tellurirenes

N. Tokitoh and W. Ando

9.5 Product Class 5:1 H-Azirines

K.-P. Zeller

9.6 Product Class 6: Phosphirenes

H. Heydt

9.7 Product Class 7: Three-Membered Rings with Phosphorus and One or More Heteroatoms

H. Heydt

9.8 Product Class 8: Four-Membered Rings with One or More Heteroatoms

M. Regitz and U. Bergsträßer

9.9 Product Class 9: Furans

B. König

9.10 Product Class 10: Thiophenes, Thiophene 1,1-Dioxides, and Thiophene 1-Oxides

J. Schatz

9.11 Product Class 11: Selenophenes

J. Schatz

9.12 Product Class 12: Tellurophenes

J. Schatz

9.13 Product Class 13: 1H-Pyrroles

D. StC. Black

9.14 Product Class 14: Phospholes

F. Mathey

Volume 10: Fused Five-Membered Hetarenes with One Heteroatom

Introduction

E. J. Thomas

10.1 Product Class 1: Benzo[b]furans

C. P. Dell

10.2 Product Class 2: Benzo[c]furans

P. G. Steel

10.3 Product Class 3: Dibenzofurans

K. Jones

10.4 Product Class 4: Benzo[b]thiophenes

C. M. Rayner and M. A. Graham

10.5 Product Class 5: Benzo[c]thiophenes

T. L. Gilchrist and S. J. Higgins

10.6 Product Class 6: Dibenzothiophenes

M. D. Andrews

10.7 Product Class 7: Benzo[b]selenophenes

P. J. Murphy

10.8 Product Class 8: Benzo[c]selenophenes

P. J. Murphy

10.9 Product Class 9: Dibenzoselenophenes

P. J. Murphy

10.10 Product Class 10: Benzo[b]tellurophenes

P. J. Murphy

10.11 Product Class 11: Benzo[c]tellurophenes

P. J. Murphy

10.12 Product Class 12: Dibenzotellurophenes

P. J. Murphy

10.13 Product Class 13: Indole and Its Derivatives

J. A. Joule

10.14 Product Class 14: 1H- and 2H-Isoindoles

T. J. Donohoe

10.15 Product Class 15: Carbazoles

P. T. Gallagher

10.16 Product Class 16: Indolizines

M. Shipman

10.17 Product Class 17: Benzo[b]phospholes

R. A. Aitken

10.18 Product Class 18: Benzo[c]phospholes

R. A. Aitken

10.19 Product Class 19: Dibenzophospholes

R. A. Aitken

10.20 Product Class 20: Phosphorus Analogues of Indolizines

R. A. Aitken

Volume 11: Five-Membered Hetarenes with One Chalcogen and One Additional Heteroatom

Introduction

E. Schaumann

11.1 Product Class 1:1,3-Dioxolium Salts and Annulated Analogues

H. Perst

11.2 Product Class 2:1,2-Oxathiolium Salts

H. Perst

11.3 Product Class 3:1,3-Oxathiolium Salts and Related Compounds

H. Perst and C. Klenke

11.4 Product Class 4:1,2-Oxaselenolium Salts

H. Perst

11.5 Product Class 5:1,3-Oxaselenolium Salts

H. Perst

11.6 Product Class 6:1,2-Oxatellurolium Compounds and Benzoannulated Analogues

H. Perst

11.7 Product Class 7:1,2-Dithiolium Salts and Related Compounds

C. Th. Pedersen

11.8 Product Class 8:1,3-Dithiolium Salts, Se and Te Analogues and Benzoannulated Analogues

G. Schukat and E. Fanghänel

11.9 Product Class 9: Isoxazoles

B. J. Wakefield

11.10 Product Class 10:1,2-Benzisoxazoles and Related Compounds

R. K. Smalley

11.11 Product Class 11: 2,1-Benzisoxazoles and Related Compounds

R. K. Smalley

11.12 Product Class 12: Oxazoles

G. V. Boyd

11.13 Product Class 13: Benzoxazoles and Other Annulated Oxazoles

G. V. Boyd

11.14 Product Class 14: 1,3-Oxaphospholes and Benzoannulated Analogues

D. Gudat

11.15 Product Class 15: Isothiazoles

D. W. Brown and M. Sainsbury

11.16 Product Class 16: Benzisothiazoles

D. W. Brown and M. Sainsbury

11.17 Product Class 17: Thiazoles

D. Kikelj and U. Urleb

11.18 Product Class 18: Benzothiazoles and Related Compounds

H. Ulrich

11.19 Product Class 19:1,2- and 1,3-Thiaphospholes and Benzoannulated Analogues

D. Gudat

11.20 Product Class 20: Isoselenazoles

W.-D. Pfeiffer

11.21 Product Class 21: Annulated Isoselenazole Compounds

W.-D. Pfeiffer

11.22 Product Class 22: Selenazoles

W.-D. Pfeiffer

11.23 Product Class 23: Annulated Selenazole Compounds

W.-D. Pfeiffer

11.24 Product Class 24:1,3-Selenaphospholes

D. Gudat

11.25 Product Class 25: Isotellurazoles, and Annulated Isotellurazole and Tellurazole Compounds

W.-D. Pfeiffer

Volume 12: Five-Membered Hetarenes with Two Nitrogen or Phosphorus Atoms

Introduction

R. Neier

12.1 Product Class 1: Pyrazoles

B. Stanovnik and J. Svete

12.2 Product Class 2: 1H- and 2H-Indazoles

W. Stadlbauer

12.3 Product Class 3: Imidazoles

M. R. Grimmett

12.4 Product Class 4: Benzimidazoles

M. R. Grimmett

12.5 Product Class 5: Azaindolizines with Two Nitrogen Atoms in the Five-Membered Ring

G. Hajos and Z. Riedl

12.6 Product Class 6: Azaphospholes and Azarsoles

A. Schmidpeter and K. Karaghiosoff

12.7 Product Class 7: Diphospholes

F. Mathey

Volume 13: Five-Membered Hetarenes with Three or More Heteroatoms

Introduction

R. C. Storr and T. L. Gilchrist

13.1 Product Class 1:1,2,5-Oxathiazoles, 1,2,3-Dithiazoles, and Related Compounds

N. G. Argyropoulos

13.2 Product Class 2:1,2,4-Dioxazoles, 1,2,4-Oxathiazoles, and 1,2,4-Dithiazoles

N. G. Argyropoulos

13.3 Product Class 3:1,3,2-Oxathiazoles, 1,3,2-Dithiazoles, and Related Compounds

N. G. Argyropoulos

13.4 Product Class 4:1,4,2-Oxathiazoles and Related Compounds

N. G. Argyropoulos

13.5 Product Class 5:1,2,3-Oxadiazoles

T. L. Gilchrist

13.6 Product Class 6:1,2,4-Oxadiazoles

K. Hemming

13.7 Product Class 7:1,2,5-Oxadiazoles

R. M. Paton

13.8 Product Class 8:1,3,4-Oxadiazoles

G. W. Weaver

13.9 Product Class 9:1,2,3-Thiadiazoles

D. J. Wilkins and P. A. Bradley

13.10 Product Class 10:1,2,4-Thiadiazoles

D. J. Wilkins and P. A. Bradley

13.11 Product Class 11:1,2,5-Thiadiazoles and Related Compounds

P. A. Koutentis

13.12 Product Class 12:1,3,4-Thiadiazoles

S. J. Collier

13.13 Product Class 13: 1,2,3-Triazoles

A. C. Tomé

13.14 Product Class 14: 1,2,4-Triazoles

A. D. M. Curtis

13.15 Product Class 15: Dithiaphospholes and Their Analogues

R. K. Bansal, N. Gupta, and S. J. Collier

13.16 Product Class 16: Oxazaphospholes and Thiazaphospholes

R. K. Bansal and Neelima Gupta

13.17 Product Class 17: Oxadiphospholes and Their Analogues

S. J. Collier

13.18 Product Class 18: Diazaphospholes and Diazarsoles

R. K. Bansal and Neelima Gupta

13.19 Product Class 19: Azadiphospholes and Their Analogues

S. J. Collier

13.20 Product Class 20: Triphospholes and Diphospharsoles

R. K. Bansal and Neelima Gupta

13.21 Product Class 21: Thiadiazaphospholes

S. J. Collier

13.22 Product Class 22: Triazaphospholes

R. K. Bansal and Neelima Gupta

13.23 Product Class 23: Diazadiphospholes

S. J. Collier

13.24 Product Class 24: Tetraphospholes

S. J. Collier

13.25 Product Class 25: Tetraazaphospholes

S. J. Collier

13.26 Product Class 26: Pentaphospholes and Pentarsoles

R. K. Bansal and Neelima Gupta

13.27 Product Class 27: Selenazoles and Tellurazoles Containing One or More Other Heteroatoms

R. A. Aitken

13.28 Product Class 28: Oxatriazoles

M. Begtrup

13.29 Product Class 29: Thiatriazoles

M. Begtrup

13.30 Product Class 30: Tetrazoles

A. F. Brigas

13.31 Product Class 31: Pentazoles

R. C. Storr

Volume 14: Six-Membered Hetarenes with One Chalcogen

Introduction

E. J. Thomas

14.1 Product Class 1: Pyrylium Salts

T. S. Balaban and A. T. Balaban

14.2 Product Class 2: Benzopyrylium Salts

M. Nógrádi

14.3 Product Class 3: Pyranones and Pyranthiones

K. Afarinkia and V. Vinader

14.4 Product Class 4: Benzopyranones and Benzopyranthiones

A. C. Williams and N. Camp

14.5 Product Class 5: 3-Oxidopyrylium Salts and Their Thio and Benzo-Fused Analogues

A. Nelson

14.6 Product Class 6: Thiopyrylium Salts

W.-D. Rudorf

14.7 Product Class 7: Benzothiopyrylium Salts

W.-D. Rudorf

14.8 Product Class 8: Thiopyranones and Thiopyranthiones

S. Faulkner, R. C. Whitehead, and R. J. Aarons

14.9 Product Class 9: Benzothiopyranones and Benzothiopyranthiones

A. Nelson

14.10 Product Class 10: Selenopyrylium and Benzoselenopyrylium Salts

P. J. Murphy

14.11 Product Class 11: Selenopyranones and Benzoselenopyranones

P. J. Murphy

14.12 Product Class 12: Telluropyrylium and Benzotelluropyrylium Salts

P. J. Murphy

14.13 Product Class 13: Telluropyranones and Benzotelluropyranones

P. J. Murphy

Volume 15: Six-Membered Hetarenes with One Nitrogen or Phosphorus Atom

Introduction

D. StC. Black

15.1 Product Class 1: Pyridines

D. Spitzner

15.2 Product Class 2: Pyridinones and Related Systems

P. A. Keller

15.3 Product Class 3: Quinolines

R. D. Larsen and D. Cai

15.4 Product Class 4: Quinolinones

R. D. Larsen

15.5 Product Class 5: Isoquinolines

M. Álvarez and J. A. Joule

15.6 Product Class 6: Isoquinolinones

M. Álvarez and J. A. Joule

15.7 Product Class 7: Quinolizinium Salts and Benzo Analogues

H. Ihmels

15.8 Product Class 8: Naphthyridines

P.-W. Phuan and M. C. Kozlowski

15.9 Product Class 9: Acridines

R. H. Prager and C. M. Williams

15.10 Product Class 10: Acridin-9(10H)-ones and Related Systems

R. H. Prager and C. M. Williams

15.11 Product Class 11: Phenanthridines

P. A. Keller

15.12 Product Class 12: Phenanthridinones and Related Systems

P. A. Keller

15.13 Product Class 13:1λ3-Phosphinines

F. Mathey and P. Le Floch

15.14 Product Class 14: 1λ5-Phosphinines

R. Streubel

15.15 Product Class 15: Benzo-Fused And Other Annulated Phosphinines

U. Bergsträßer

Volume 16: Six-Membered Hetarenes with Two Identical Heteroatoms

Introduction

Y. Yamamoto

16.1 Product Class 1:1,2-Dioxins and Benzo- and Dibenzo-Fused Derivatives

M. Matsumoto

16.2 Product Class 2:1,4-Dioxins and Benzo- and Dibenzo-Fused Derivatives

M. Matsumoto

16.3 Product Class 3:1,2-Dithiins

R. Sato

16.4 Product Class 4:1,4-Dithiins

R. Sato

16.5 Product Class 5:1,2-Diselenins

R. Sato

16.6 Product Class 6:1,4-Diselenins

R. Sato

16.7 Product Class 7:1,4-Ditellurins

R. Sato

16.8 Product Class 8: Pyridazines

N. Haider and W. Holzer

16.9 Product Class 9: Cinnolines

N. Haider and W. Holzer

16.10 Product Class 10: Phthalazines

N. Haider and W. Holzer

16.11 Product Class 11: Pyridazino[1,2-a]pyridazines

N. Haider and W. Holzer

16.12 Product Class 12: Pyrimidines

S. von Angerer

16.13 Product Class 13: Quinazolines

D. Kikelj

16.14 Product Class 14: Pyrazines

N. Sato

16.15 Product Class 15: Quinoxalines

S. Gobec and U. Urleb

16.16 Product Class 16: Phenazines

U. Urleb and S. Gobec

16.17 Product Class 17: Purines

F. Seela, N. Ramzaeva, and H. Rosemeyer

16.18 Product Class 18: Pyridopyridazines

M. Sako

16.19 Product Class 19: Pyridopyrimidines

M. Sako

16.20 Product Class 20: Pyridopyrazines

M. Sako

16.21 Product Class 21: Pteridines and Related Structures

T. Ishikawa

16.22 Product Class 22: Other Diazinodiazines

T. Ishikawa

16.23 Product Class 23: Diphosphinines

M. Yoshifuji and S. Ito

Volume 17: Six-Membered Hetarenes with Two Unlike or More than Two Heteroatoms and Fully Unsaturated Larger-Ring Heterocycles

Introduction

S. M. Weinreb and Y. R. Mahajan

17.1 Product Class 1: Six-Membered Hetarenes with Two Unlike Heteroatoms

17.1.1 Product Subclass 1: Two Unlike Oxygen, Sulfur, Selenium, or Tellurium Atoms

S. Yamazaki and K. Yamamoto

17.1.2 Product Subclass 2: One Oxygen and One Nitrogen or Phosphorus Atom

H. Ulrich

17.1.3 Product Subclass 3: One Sulfur, Selenium, or Tellurium Atom and One Nitrogen or Phosphorus Atom

H. Ulrich

17.2 Product Class 2: Six-Membered Hetarenes with Three Heteroatoms

17.2.1 Product Subclass 1: 1,2,3-Triazines and Phosphorus Analogues

H. Döpp and D. Döpp

17.2.2 Product Subclass 2: 1,2,4-Triazines

C. W. Lindsley and M. E. Layton

17.2.3 Product Subclass 3: 1,3,5-Triazines and Phosphorus Analogues

S. von Angerer

17.3 Product Class 3: Six-Membered Hetarenes with More Than Three Heteroatoms

M. Bohle

17.4 Product Class 4: Seven-Membered Hetarenes with One Heteroatom

17.4.1 Product Subclass 1: Oxepins

S. von Angerer

17.4.2 Product Subclass 2: Benzoxepins

S. von Angerer

17.4.3 Product Subclass 3: Thiepins and Selenium Analogues

A. L. Schwan

17.4.4 Product Subclass 4: Benzothiepins and Selenium/Tellurium Analogues

A. L. Schwan

17.4.5 Product Subclass 5: Azepines, Cyclopentazepines, and Phosphorus Analogues

M. D. Surman and R. H. Hutchings

17.4.6 Product Subclass 6: Benzazepines and Their Group 15 Analogues

J.-P. K. Meigh

17.5 Product Class 5: Seven-Membered Hetarenes with Two or More Heteroatoms

R. J. Herr

17.6 Product Class 6: Eight- and Nine-Membered Hetarenes and Heteroannulenes with One or More Heteroatoms

R. M. Borzilleri

17.7 Product Class 7: Cyclazines

Y. Tominaga

17.8 Product Class 8: Porphyrins and Related Compounds

K. M. Smith and M. G. H. Vicente

17.9 Product Class 9: Phthalocyanines and Related Compounds

N. B. McKeown

Structure Index

This index comprises a list of key structures from the Hetarenes and Related Ring Systems series.

To use the index you first need to identify the following four characteristics for the ring system you are interested in:

(1) whether the system is monocyclic, bicyclic etc. (see page header)

(2) the ring size i.e. 3-membered, 4-membered etc. (see left-hand column)

(3) the number of heteroatoms within the ring system (see number to the left of illustrated row of structures)

(4) heteroatoms are prioritized in the following order: O, S, Se, Te, N, P, As, Sb, Bi, (Zr)

Having identified the ring system of interest please refer to the number beneath the structure in order to determine the relevant volume number (small and bold) and page number within the series.

Name Reaction Index

A

Achmatowicz

– Achmatowicz oxidative ring expansion 14-643

– Achmatowicz ring expansion 14-639, 14-643

Adam’s catalyst

– Adam’s catalyst 10-745, 16-305

Akabori method

– Akabori method 12-356, 12-426

Alder-Longo reaction

– Alder-Longo approach 17-1116

Alder-Rickert cleavage

– Alder-Rickert cleavage 09-222

aldol reaction

– aldol condensation 10-104, 10-105, 10-399, 10-601, 15-692, 15-806, 15-898

– aldol process 09-477

– aldol reaction 09-477, 10-494, 13-168, 14-793f., 14-802f.

– aldol-type condensation 10-450, 10-620, 12-595

Algar-Flynn-Oyamada oxidation

– Algar-Flynn-Oyamada oxidation 14-503

Allen-Robinson reaction

– Allen-Robinson reaction 14-447

Amadori rearrangement

– Amadori rearrangement 16-1302f.

ANRORC

– ANRORC 14-11f.

– SNANRORC mechanism 15-237, 15-791

– SN-ANRORC 16-1191, 16-1209

Appel’s salt

– Appel’s salt 13-13-13-16

Arbusov reaction

– Arbusov reaction 10-450, 13-174, 14-702

– Arbusov-type transformation 10-100

Arduengo

– Arduengo-type carbene 13-734

Arnold’s reagent

– Arnold’s reagent 16-1043

Auwer’s rule

– Auwer’s rule 12-85

B

Baeyer-Villiger oxidation

– Baeyer-Villiger cleavage 10-535, 10-624

– Baeyer-Villiger oxidation 10-582, 10-617, 14-415f., 14-586f., 15-1056

– Baeyer-Villiger reaction 14-586f.

Baker’s rule

– Baker’s trans rule 16-1034

Baker-Venkataraman rearrangement

– Baker-Venkataraman rearrangement 14-407, 14-509

Balaban-Nenitzescu-Praill reaction

– Balaban-Nenitzescu-Praill reaction 14-25f.

Balz-Schiemann reaction

– Balz-Schiemann reaction 16-818, 16-894

Bamberger degradation

– Bamberger degradation 12-374

Barbier reaction

– Barbier’s method 15-1129

– Barbier-type reaction 16-281

Bartoli synthesis

– Bartoli indole synthesis 10-385

– Bartoli synthesis 10-384

Barton-Zard reaction

– Barton-Zard reaction 09-489, 09-491

Baylis-Hillman reaction

– Baylis-Hillman acetate 15-396

– Baylis-Hillman adduct 15-434, 15-500, 15-563

– Baylis-Hillman reaction 10-761, 14-410

Beckmann fragmentation

– Beckmann fragmentation 13-329f. Beckmann rearrangement

– Beckmann rearrangement 10-75, 10-258, 10-582, 10-593, 10-739f., 11-293, 11-295, 11-489, 11-582, 11-773, 11-807, 11-869, 11-985, 11-986, 12-567, 13-131, 13-186, 15-8, 15-631, 15-722, 15-724, 15-740, 15-1092, 16-775, 17-45, 17-872, 17-873, 17-875, 17-1017f.

– Beckmann-type rearrangement 17-509

Begtrup and Larsen reaction

– Begtrup and Larsen approach 12-489

– Begtrup and Larsen quaternization 12-463

Begtrup method

– Begtrup method 12-464, 12-495

– Begtrup two-stage method 12-495

Beirut reaction

– Beirut reaction 16-866, 16-925

benzoin reaction

– benzoin reaction 12-502

Bernthsen reaction

– Bernthsen condensation 15-998

– Bernthsen procedure 15-997, 15-1023

– Bernthsen reaction 15-997, 15-1023

– Bernthsen synthesis 15-997

– Bernthsen’s method 17-163, 17-164

– Bernthsen’s thiosulfate method 17-163, 17-164

Beyer modification (Doebner-von Miller reaction)

– Beyer modification 15-391

– Beyer-like reaction 15-511

Beyer-Combes synthesis

– Beyer-Combes synthesis 15-440f.

Birch reduction

– Birch reduction 10-131, 10-212, 15-189

– Birch reduction conditions 10-212

– Birch-type reduction 15-949

Bird’s aromaticity index

– Bird’s aromaticity index 10-653

Bischler synthesis

– Bischler indole synthesis 10-390

– Bischler process 10-462

– Bischler synthesis 10-390, 17-357, 17-382

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