Turkish Journal of Chemistry
DOI
-
Abstract
Chloride 18 (47%) and alcohol 21 (44%) were isolated from the reaction of alcohol 20 with SOCl_2. Cyclopropylcarbinyl -- cyclopropylcarbinyl rearrangement leads to chloride 22, which hydrolyses on separation to give alcohol 21. Chloride 18 results from cyclopropyl -- allylcarbinyl rearrangement, followed by a 1,2 -- aryl shift (sequential rearrangement). Syntheses of compounds 23 and 24 support the structures. The behaviour of 20 differs from that of exo isomer 14, probably due to the nature of the intermediates in these reactions.
Keywords
Alcohols, Benzohomonorbornadiene, Halogenation, Rearrangement, Thionyl chloride
First Page
141
Last Page
148
Recommended Citation
MENZEK, ABDULLAH and KARAKAYA, MELEK (2004) "Cationic Rearrangements of an endo}-Cyclopropyl Methanol System Incorporated in a Benzonorbornadiene System," Turkish Journal of Chemistry: Vol. 28: No. 2, Article 1. Available at: https://journals.tubitak.gov.tr/chem/vol28/iss2/1
