3-Thiabicyclo [3.2. 0] hept-6-ene 3, 3-dioxide: a novel synthon for cis-1, 2-divinyl intermediates and derived seven-membered ring systems

RA Aitken, JIG Cadogan, I Gosney, BJ Hamill…

Index: Aitken, R. Alan; Cadogan, J. I. G.; Gosney, Ian; Hamill, Brendan J.; McLaughlin, Leo M. Journal of the Chemical Society, Chemical Communications, 1982 , # 20 p. 1164 - 1165

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Abstract

Functionalisation of the 6,7-double bond in the novel bicyclic sulphone, 3-thiabicyclo[3.2.0] hept-6-ene 3,3-dioxide, followed by thermal extrusion of SO2, allows direct entry into seven -membered ring systems via a Cope rearrangement of the resulting cis-I ,2-divinyl intermediates. ... A lack of regio-control in the functionalisation of the central double bond in cis-hexa- I ,3,5-triene frustrates what is con- ceptually an attractive and potentially general ...