THERMAL REARRANGEMENT OF DIVINYLCYCLOPROPANE SYSTEMS. PREPARATION OF FUNCTIONALIZED, STEREOCHEMICALLY DEFINED BICYCLIC AND TRICYCLIC PRODUCTS CONTAINING THE BICYCLOOCTANE SKELETON

Article abstract of DOI:10.1016/0040-4039(84)80040-4

A study involving the preparation and thermolysis of substituted 6-exo-(1-alkenyl)bicyclo<3.1.0>hex-2-ene systems (14, 15, 23, 29, 40) shows (a) that C-8 functionalized bicyclo<3.2.1>octa-2,6-dienes can be prepared readily via this methodology (14 -> 16; 15 -> 17), (b) that the rearrangement reaction is stereospecific even when the 6-(1-alkenyl) group is substituted with a sterically bulky isopropyl group (23 -> 24; 29 -> 30), and (c) that the method can be extended to include the preparation of tricyclic systems (40 -> 41).