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An Oxidative Rearrangement of 6-Phenylbicyclo[3.2.0]heptan-6-ol to 1,1′-Biphenyl-Carbaldehydes: A Mechanistic Study

✍ Scribed by Mustafa Ceylan; Esra Fındık; Hasan Seçen

Publisher: John Wiley and Sons
Year: 2008
Tongue: German
Weight: 203 KB
Volume: 91
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.200890058

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✦ Synopsis

Abstract

Acid‐catalyzed rearrangement of 6‐phenylbicyclo[3.2.0]heptan‐6‐ol gave 1,1′‐biphenyl and 1,1′‐biphenyl‐carbaldehydes in small amounts as well as the expected rearrangement products. A detailed study of the reaction mechanism revealed that the conversion occurs via an oxidative process through the consecutive formation of cycloheptadienes, cycloheptatrienes, and 1,1′‐biphenyls. The acid‐catalyzed rearrangement of 6‐phenylbicyclo[3.2.0]hept‐2‐en‐6‐ols gave 1‐ and 2‐phenylcycloheptatrienes directly, from which 1,1′‐biphenyl and 1,1′‐biphenyl‐carbaldehydes were obtained by oxidation.

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## Abstract Treatment of 2,2,4,4‐tetramethyl‐1,5‐diphenyl‐6,7‐dithiabicyclo[3.1.1]heptane 6‐endo‐oxide (2) with Montmorillonitc K 10 in dichloromethane gave 2,2,‐4,4‐tetramethyl‐1,5‐diphenyl‐7,8‐dithia‐6‐oxabicyclo‐[3.2.1]octane (6) (11%) with recovery of 2 (87%). Under similar reaction conditions,