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Synthesis and use of new substituted 1,3,5-hexatrienes in studying thermally induced 6n-electrocyclizations

Sunnemann, Hans Wolf; Banwell, Martin; de Meijere, Armin


An acyclic, two heterocyclic, and two bicyclic alkenylstannanes, 3, 4a, 4b, 8 and 11, respectively, were synthesized in yields ranging from 43 to 97 %, and each was subjected to a sequence of Stille and Heck couplings with 2-bromocyclohexenyl triflate (13) and alkyl (tert-butyl and methyl) acrylate to furnish seven new 1,3,5-hexatrienes 19, 20, 21, 22-tBu, 22-Me, 23 and 43, respectively, in 58-84 % yields. For the alkenylstannanes 4a,b, 8 and 11, customized combinations of catalysts had to be...[Show more]

CollectionsANU Research Publications
Date published: 2007
Type: Journal article
Source: European Journal of Organic Chemistry
DOI: 10.1002/ejoc.200700201


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