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The chemistry of cycloheptatriene: Part II: Reduction of cycloheptatriene to cycloheptadiene and cycloheptene

✍ Scribed by A. P. Ter Borg; A. F. Bickel

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
243 KB
Volume
80
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

Reduction of cycloheptatriene (I) and cycloheptadiene (II) with 2 equivalents of sodium in liquid ammonia yields ‐ after addition of ethanol ‐ cycloheptadiene and cycloheptene (III), respectively.

These reactions proceed via coloured intermediates. Reduction of I with 4 equivalents of sodium gives only III.

Carbonation of the reaction mixture of I and 2 equivalents of sodium yields a cycloheptadiene monocarboxylic acid whereas no carboxylic acid has formed upon carbonation of the reaction mixture of II and 2 equivalents of sodium.

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## Abstract Addition of dichlorocarbene to cyclopentadiene yields chlorobenzene. The addition of dichlorocarbene to cycloheptatriene yields 8,8‐dichloro‐bicyclo [5.1.0] octadiene‐2,4 (II). When (II) is heated at 140Β° a rearrangement to 1‐chlorobenzocyclobutene (III) occurs with evolution of HCl. Re

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## Abstract Tropylium perchlorate and fluoroborate have been prepared by the autoxidation of cycloheptatriene dissolved in acetic acid containing perchloric or fluoroboric acid, respectively. An optimum yield of 60 % (calculated on the strong acid) is obtained by employing twice as much cycloheptat