Synthesis of Acetilenes, allenes and Cumulenes

Автор(ы):Brandsma L., Verkruijsse H. D.
Год изд.:1981
Описание: In 1971 we published "Preparative Acetylenic Chemistry", a collection of procedures for various acetylenic compounds. An important aim of this book was to make acetylenes more accessible, so that barriers for starting research in this field could be lowered. The experimental work for the present book was started some years ago. It involved checking procedures from the literature and developing new ones, in some cases based on very concise instructions in preliminary papers. Most of the preparations in this book required more or less extensive research in order to find procedures for synthesizing the compounds on a reasonable scale. Important aspects of this research were monitoring the conversions, in order to avoid undesirably long reaction times, and searching for efficient methods of isolation. A number of methods from the literature which seemed attractive at first sight, are not exemplified in this book, either because they could not be reproduced at all by us or because they appeared to be impractical when performed on a larger scale (0.1-0.2 molar).
Synthesis of Acetilenes, allenes and Cumulenes — обложка книги. Обложка книги.
Chapter I. Reaction vessels and some special procedures [1]
  General remarks and abbreviations [3]
Chapter II. Conversion of acetylenes and cumulenes into anionic and organometallic intermediates [7]
  1. Acidity of acetylenes and cumulenes and stability of their anions [7]
  2. Organometallic reagents and strong bases [9]
  3. Experiments [11]
Chapter III. Oerivatization of acetylenes and cumulenes [27]
  1. Functionalization with various electrophilic reagents [27]
  2. Experiments [28]
Chapter IV. Base-promoted interconversions between acetylenes and cumulenes [87]
  1. Isomerizations with catalytic amounts of base [87]
  2. Isomerizations via an anionic or organometallic intermediate [87]
  3. Experiments [89]
Chapter V. Synthesis of acetylenes and cumulenes by elimination reactions [115]
  1. 1,2-Dehydrohalogenation [115]
  2. 1,4- and 1,6-Eliminations [115]
  3. 1,1-Dehalogenation of geminal dihalocyclopropyl derivatives [117]
  4. 1,2-Dehalogenation and 1,4-dehalogenation [118]
  5. Experiments [119]
Chapter VI. Synthesis of acetylenes and cumulenes by 1,3-substitution reactions [151]
  1. Introduction [151]
  2. Nucleophilic 1,3-substitutions [151]
  3. Electrophilic 1,3-substitutions [156]
  4. Experiments [157]
Chapter VII. Miscellaneous syntheses [197]
  1. 2,3-Sigmatropic rearrangements [197]
  2. 3,3-Sigmatropic rearrangements [200]
  3. Additions to unsaturated systems [206]
Chapter VIII. Transformation of functional groups in acetylenes and cumulenes [213]
  1. Unsaturated sulfoxides and sulfones [213]
  2. Acetylenic halides [215]
  3. Acetylenic esters and dithioesters [222]
  4. Acetylenic and allenic nitriles and thiocyanates [225]
  5. Acetylenic amines [228]
  6. Acetylenic ethers, selenides and ketones [231]
Type Index [239]
Formula Index [243]
NMR—parameters of the Aliens Moiety [253]
References [271]
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