Carbene Chemistry

Carbene Chemistry, Second Edition discusses the developments in various areas of carbene chemistry, including the correlation of spectroscopic studies of isolated carbenes with quantum chemical calculations; new carbene precursors; differentiation of carbenes and carbenoids; and mechanisms of single and triplet carbine reactions.
This book is composed of two main parts encompassing 13 chapters. The first part covers the many reactions known to transfer a formally divalent carbon fragment from one molecule to another, with special emphasis on the mechanism and a critical evaluation of the evidence for carbene intermediates. The second part examines the multitude of product-forming reactions of carbenes and carbenoids with various substrates. This part also describes the structure-reactivity relationships for both carbenes and their substrates, followed by a discussion of the applications of carbene compounds in synthetic organic chemistry.
This work will be of great value to organic chemists and researchers.

Inhalt
Preface to Second Edition

Preface to First Edition


Part I Methylene Transfer Reactions


Chapter 1 Introduction


I. Examples of Methylene Transfer


II. Mechanisms of Methylene Transfer


III. Carbenes and Carbenoids


Review Literature On Carbenes


Chapter 2 Photochemical and Thermal Methylene Transfer Reactions


I. Photolysis of Ketene


II. Photolysis of Alkyl- and Arylketenes


III. Photolysis of Carbon Suboxide


IV. Photolysis of Diazo Compounds


V. Pyrolysis of Diazo Compounds


VI. Bamford-Stevens Reaction


VII. Decomposition of Diazirines


VIII. Decomposition of Cyclopropanes


IX. Photolysis of Oxiranes


X. Pyrolysis of 7-Norbornadienone Ketals


XI. Rearrangement of Carbonyl Compounds


XII. Decomposition of Polyhalomethanes


XIII. Decomposition of Alkanes


XIV. Reactions of Atomic Carbon


XV. Decomposition of Olefins


XVI. Desulfurization and Deoxygenation Reactions


XVII. Decomposition of Ylides


References


Chapter 3 Organometallic Methylene Transfer Agents


I. Catalytic Decomposition of Diazoalkanes


II. Simmons-Smith Reaction


III. Organolithium Reagents


IV. Organomercury Reagents


V. Organosilicon and Organotin Reagents


VI. Carbene Complexes of the Transition Metals


References


Chapter 4 Base-Induced a-Elimination


I. Basic Hydrolysis of Haloforms


II. Trihalomethides in Aprotic Media


III. a-Elimination at Methylene Halides


IV. Dehydrohalogenation of Benzylic Halides


V. Solvolysis of Propargyl and Allenyl Halides


VI. a-Elimination at Alkyl Halides


VII. Deprotonation of Carbonium Ions


References


Part II Structure and Reactivity of Carbenes and Carbenoids


Chapter 5 the Structural Theory of Carbenes


I. An Approach To the Electronic Structure Of Carbenes


II. the Electronic Structure of CH2


III. Use of Extended Hückel Theory in the Elucidation of Carbene Structure


IV. Halocarbenes


V. Charge Distribution


VI. Conclusions


References


Chapter 6 the Spectra of Carbenes


I. Electronic and Vibration-Rotation Spectroscopy


II. Electron Spin Resonance (ESR) Spectroscopy


References


Chapter 7 Reactions with Carbon-Hydrogen Bonds


I. Insertion and Abstraction Mechanisms


II. Stereochemistry


III. Selectivity


IV. Intramolecular Insertion


References


Chapter Addition to Alkenes


I. Stereospecificity


II. Stereoselectivity


III. Reactivity


IV. Synthesis of Cyclopropanes


V. Addition Accompanied By Rearrangement


VI. Intramolecular Addition


References


Chapter 9 Addition to Alkynes


I. Formation of Cyclopropenes


II. Formation of Bicyclobutanes


III. Reactions with Enynes


IV. Addition Accompanied By Rearrangement


V. "1,3-Dipolar Additions" of Carbonylcarbenes


VI. Thermal Reactions of Dialkyl Acetylene Dicarboxylates


References


Chapter 10 Addition to Arenes


I. Aromatic Carbocyclic Compounds


II. Aromatic Heterocyclic Compounds


III. Intramolecular Reactions


References


Chapter 11 Reactions Involving Hetero Atoms


I. Sllanes and Germanes


II. Nitrogen Compounds


III. Organophosphorus Compounds


IV. Oxygen Compounds


V. Organosulfur Compounds


VI. Organic Halides


VII. Organometallic Compounds


References


Chapter 12 Rearrangements


I. 1,2 Shifts in Alkylcarbenes


II. Cyclopropylidene-Allene Rearrangement


III. Rearrangement and Fragmentation of Cyclopropylcarbenes


IV. Cyclobutylidene-Methylenecyclopropane Rearrangement


V. Wolff Rearrangement of Diazo Ketones


VI. Rearrangement of Arylcarbenes


References


Chapter 13 Silicon, Germanium, AND Tin Structural Analogs of Carbenes


I. Introduction


II. Silicon Dichloride, :SiCl2


III. Silicon Dibromide and Diiodide, SiBr2 and SiI2


IV. Chlorosilyene and Bromosilyene, HSiCl and HSiBr


V. Silicon Difluoride, SiF2


VI. Silylene, SiH2


VII. Silicon Atoms, Si


VIII. Alkyl- and Arylsilylenes, RSiH and RR'Si


IX. Silicon Monoxide and Silicon Monosulfide, SiO and SiS


X. Germanium Atoms, Ge


XI. Germylene, GeH2


XII. Dialkyl and Diaryl Germylenes, R2Ge


XIII. Germanium Dihalides, GeX2


XIV. Germanium Monoxide and Monosulfide, GeO and GeS


XV. Divalent Tin Compounds


XVI. Conclusion


References


Author Index


Subject Index

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