Studies in sesquiterpenes—LVII: isolongifolene (part 8): solvolysis of 8-bromoneoisolongifolene

Yadav, J. S. ; Chawla, H. P. S. ; Dev, Sukh (1978) Studies in sesquiterpenes—LVII: isolongifolene (part 8): solvolysis of 8-bromoneoisolongifolene Tetrahedron, 34 (4). pp. 475-480. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/0...

Related URL: http://dx.doi.org/10.1016/0040-4020(78)80037-4

Abstract

Acetolysis of 8-bromoneoisolongifolene generates, besides two normal products (of elimination and SN2 displacement), which were minor, one rearranged elimination product and a tertiary acetate. The rearranged diolefine arises from acetic acid-catalysed rearrangement of the normal elimination product, while the tertiary acetate is a Wagner substitution product arising from a syn-migration. In this context various factors controlling such migrations are discussed and, the possible role of energetics of the incipient carbonium ion at the migration origin highlighted.

Item Type:Article
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ID Code:64532
Deposited On:08 Oct 2011 12:28
Last Modified:11 Jul 2012 18:23

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