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The chemistry of cycloheptatriene: Part I. Synthesis of benzocyclobutene

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

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

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✦ Synopsis

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 140° a rearrangement to 1‐chlorobenzocyclobutene (III) occurs with evolution of HCl. Reduction of (III) with hydrogen in the presence of palladium gives benzocyclobutene (V).

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