Electronic control of stereoselectivity. 9. The stereochemical course of electrophilic additions to aryl-substituted benzobicyclo [2.2. 2] octadienes

LA Paquette, F Bellamy, GJ Wells…

Index: Paquette, Leo A.; Bellamy, Francois; Wells, Gregory J.; Boehm, Michael C.; Gleiter, Rolf Journal of the American Chemical Society, 1981 , vol. 103, # 24 p. 7122 - 7133

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Citation Number: 39

Abstract

Abstract: Product and relative reactivity data have been obtained for the photooxygenation, epoxidation, cyclopropanation, oxymercuration, and hydroboration of three differently substituted (aryl) 2-methylbenzobicyclo [2.2. 2] octadienes. Syn stereoselectivity was observed in every case, with the level of syn attack being highest with the tetrafluoro derivative 2c (except in the Simmons-Smith reaction where a single isomer was produced ...