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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Attempted Synthesis of a Highly Strained Bicyclic Alkyne: Reaction of 8-Chloro-6,9-Dihydro-5,9-Methano-5h-Benzocycloheptene With Potassium T-Butoxide and an Anomalous Substitution Reaction at a Vinyl System

F Tumer, Y Taskesenligil, A Dastan and M Balci

Australian Journal of Chemistry 49(5) 599 - 603
Published: 1996

Abstract

Treatment of alkene (9) with N- bromosuccinimide gave a mixture of monobromides [(10) and (11)] which were hydrolysed to the corresponding exo alcohol (13). Oxidation of (13) and subsequent hydrogenation of unsaturated ketone (14) afforded the ketone (15). Ketone (15) was treated with PCl5, followed by potassium t- butoxide to give chloro alkene (8b). Reaction of (8b) with potassium t- butoxide resulted in the formation of unexpected allyl ether (18) whose formation mechanism has already been discussed.

https://doi.org/10.1071/CH9960599

© CSIRO 1996

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