Synthesis and solvolytic reactivity of 8-tricyclo [3.2. 1.0] octane derivatives

JS Haywood-Farmer, RE Pincock

Index: Haywood-Farmer,J.S.; Pincock,R.E. Journal of the American Chemical Society, 1969 , vol. 91, # 11 p. 3020 - 3028

Full Text: HTML

Citation Number: 30

Abstract

Abstract: To investigate the stereochemical influence of a cyclopropyl group on carbonium ion formation in a homoallylic position, the four stereoisomers (Le., exo-anti, exo-syn, endo- anti, and endo-syn) of tricyclo [3.2. 1. 02r4]-octan-8-01 were synthesized and their p- nitrobenzoates (p-NB) or p-bromobenzenesulfonates (brosylates) were solvolyzed. Reaction of 5, 5-dimethoxy-l, 2, 3, 4-tetrachlorocyclopentadiene with cyclopropene gave the endo ...