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Further evidence for the formation of butalene in the reaction of 1-chloro-[2.2.0]bicyclohexa-2,5-dienes[dewar chlorobenzenes] with a strong base

✍ Scribed by Ronald Breslow; Pyare Lal Khanna

Publisher: Elsevier Science
Year: 1977
Tongue: French
Weight: 187 KB
Volume: 18
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)83258-5

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✦ Synopsis

We have described the reaction of 1-chloro-[2.2.0]bicyclohexa-2,5-diene (I) with lithium dialkylamides to afford dialkylanilines. 1 The critical finding with regard to the mechanism of this change is that the reaction of I with lithium dimethylamide in Me2ND in the presence of diphenylisobenzofuran (DPIBF) afforded a modest yield of 1II.l This led us to conclude that butalene (II) is an intermediate in this reaction, and thus presumably in the reaction sequence without trapping reagent which affords dimethylaniline.

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