Nitrogen, Oxygen and Sulfur Ylide Chemistry,9780198500179

Nitrogen, Oxygen and Sulfur Ylide Chemistry

by
Edition: 1st
ISBN13: 9780198500179
ISBN10: 0198500173
Format: Hardcover
Pub. Date: 2002-09-26
Publisher(s): Oxford University Press
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Summary

This volume describes some of the more general and important methods for the generation of oxygen, nitrogen and sulfur ylides, and the use of these reactive intermediates for the synthesis of complex organic compounds. It includes complete practical details required to perform such reactions,and is suitable for those with no previous experience of ylide chemistry.Few recent texts have focused upon this rapidly expanding area of organic synthesis, and none provide the wealth of practical advice and experimental details that this book makes available to the non-expert.

Table of Contents

List of contributors
xi
Abbreviations xv
Nitrogen, oxygen and sulfur ylides: an overview
1(114)
J. Stephen Clark
Introduction
1(1)
Ammonium ylides
1(21)
Oxonium ylides
22(18)
Sulfonium and oxosulfonium ylides
40(17)
Azomethine ylides
57(19)
Carbonyl ylides
76(12)
Thiocarbonyl ylides
88(5)
Nitrile ylides
93(5)
References
98(17)
Ammonium, oxonium and sulfonium ylides
115(72)
Generation of ammonium ylides from metal carbenoids
115(19)
Frederick G. West
J. Stephen Clark
Introduction
115(1)
Intermolecular addition of tertiary amines to metal carbenes
116(2)
Intramolecular addition of tertiary amines to metal carbenes
118(10)
Diastereoselective ammonium ylide formation and chirality transfer
128(5)
References
133(1)
Generation of ammonium ylides by desilylation of α-silyl ammonium salts
134(7)
Yoshiro Sato
Introduction
134(1)
Benzylammonium N-alkylides
134(6)
References
140(1)
Catalytic generation and reactions of oxygen and nitrogen ylides
141(12)
Michael P. Doyle
David C. Forbes
Introduction
141(1)
Nitrogen ylides
142(4)
Oxygen ylides
146(6)
References
152(1)
Generation of sulfonium ylides by desilylation of α-silyl sulfonium salts
153(3)
Yoshiro Sato
References
155(1)
Generation of sulfur ylides from metal carbenoids
156(7)
Huw M. L. Davies
Introduction
156(1)
Diazo transfer agents
157(3)
Rhodium(II) acetate-catalysed decomposition of diazo compounds in the presence of thioethers
160(2)
Thermal rearrangement of cyclic sulfur ylides containing two electron-withdrawing groups
162(1)
References
162(1)
Generation of sulfonium ylides from carbenes and carbenoids
163(16)
Wataru Ando
Haruo Matsuyama
Introduction
163(1)
Stable sulfonium ylides generated fron carbenes
164(7)
Sulfonium ylides generated from carbenes
171(5)
Synthetic applications of [2,3]-rearrangement reactions of ylidic intermediates
176(2)
References
178(1)
Generation of oxosulfonium ylides from carbenes and carbenoids
179(8)
Wataru Ando
Haruo Matsuyama
Introduction
179(1)
Stable oxosulfonium ylides generated from carbenes
180(4)
References
184(3)
Azomethine, carbonyl and thiocarbonyl ylides
187(92)
Generation of azomethine ylides from carbenes and carbenoids
187(9)
Romuald Bartnik
Introduction
187(1)
Generation of azomethine ylides from Schiff bases
187(4)
Generation of azomethine ylides from N-H-imines
191(2)
Generation of azomethine ylides from pyridines
193(3)
References
196(1)
Generation of non-stablized azomethine ylides by sequential two-electron oxidative double desilylation of α,α'-bis(trimethylsilylmethyl)alkylamines
196(8)
Ganesh Pandey
Smita R. Gadre
Introduction
196(5)
Construction of x-azabicyclo(m.2.1)alkane frameworks by [3 + 2]-cycloaddition of cyclic azomethine ylides
201(1)
Construction of 1-azabicyclo(m.3.0)alkane frameworks
202(1)
References
203(1)
Generation of azomethine ylides by condensation of aldehydes with N-substituted α-amino esters
204(5)
M. Nyerges
L. Toke
References
208(1)
Generation of non-stabilized azomethine ylides by decarboxylative condensation of aldehydes with N-substituted α-amino esters
209(4)
M. Nyerges
L. Toke
References
212(1)
Generation of carbonyl ylides from thermally or photochemically generated carbenes
213(5)
Hideo Tomioka
References
217(1)
Generation of carbonyl ylides by intramolecular reaction of metal carbenoids: an approach to tigliane and daphnane diterpenoids
218(11)
Dennis L. Wright
Mark C. McMills
Introduction
218(1)
Synthesis of an unfunctionalized oxo-bridged tigliane
219(9)
Cyclization of other substrates
228(1)
References
228(1)
Reactions of 2-benzopyrylium-4-olate generated from intramolecular carbene--carbonyl reactions
229(8)
Toshikazu Ibata
Kazuaki Fukushima
References
236(1)
Generation and intermolecular [3 + 2]-cycloaddition of non-stabilized carbonyl ylides
237(9)
Akira Hosomi
Makoto Hojo
Hidenori Aihara
Introduction
237(1)
Generation and reactions of symmetrically dialkyl-substituted carbonyl ylides
238(3)
Generation and reactions of the parent unsubstituted and alkyl-substituted carbonyl ylides
241(5)
References
246(1)
Generation of isomunchones from metal carbenoids
246(11)
Martin E. Maier
References
256(1)
Generation and reaction of mesoionic anhydro-4-hydroxy-1,3-oxazolium hydroxide (isomunchnone) and anhydro-4-hydroxy-1,3-dioxolium hydroxide
257(8)
Toshikazu Ibata
Kazuaki Fukushima
References
264(1)
Generation and reactions of thiocarbonyl ylides derived from metal carbenoids
265(6)
Toshikazu Ibata
Kazuaki Fukushima
References
270(1)
Generation of thiocarbonyl ylides by elimination of nitrogen from 2,5-dihydro-1,3,4-thiadiazoles (Δ-1,3,4-thiadiazolines)
271(8)
Grzegorz Mloston
References
277(2)
Nitrile ylides
279(14)
Generation of nitrile ylides by the reaction of carbenes or carbenoids with nitriles
279(7)
Toshikazu Ibata
Kazuaki Fukushima
Introduction
279(1)
Formation of oxazoles
279(5)
1,3-Dipolar cycloaddition reactions of nitrile ylides
284(1)
References
285(1)
Generation of nitrile ylides by thermolysis of 1,2,4-oxazaphospholines
286(7)
Klaus Burger
Annett Fuchs
Introduction
286(1)
Synthesis of nitrile ylides from 1,2,4-oxazaphospholines
286(6)
References
292(1)
Index 293

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