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Stereochemistry of an Ene Reaction Involving 1,7-Dienes; Bicyclo[3.3.1]nonanes from (3-Cyclohexenyl)diallylcarbinols

✍ Scribed by Alan F. Thomas; Marina Lander-Schouwey

Publisher: John Wiley and Sons
Year: 1984
Tongue: German
Weight: 632 KB
Volume: 67
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19840670124

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✦ Synopsis

3-Cyclohexenyl)diallylcarbinols undergo a thermal retro -ene reaction to give crotonylcyclohexenes at ca. 200". A side-reaction is an ene reaction to give bicyclo[3.3. llnonanes. These become the main products above 300". The stereochemistry of 2-allyl-1,4,6-trimethylbicyclo[3.3.l]-6-nonen-2-ols and related compounds is discussed, and a case is described in which the ally1 group is not freely rotating.

Introduction. -One route for the preparation of the useful perfume substances 1-(1,3-dimethyl-3-cyclohexenyl)-2-buten-1-one (1) and 1-(1,4-dimethyl-3-cyclohexenylj-2-buten-1-one (2) involves the reaction of allylmagnesium chloride with the products 3, 4, of a Diels-Alder reaction between isoprene and methyl methacrylate [l] (Scheme I ) . The initial compounds formed are the diallyl compounds 5 and 6, and Scheme 1

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