The Journal of Organic Chemistry

Synthesis of adamantane derivatives by bridgehead radical addition to electron-deficient unsaturated bonds

M Ohno, K Ishizaki, S Eguchi

Index: Ohno, Masatomi; Ishizaki, Kenichi; Eguchi, Shoji Journal of Organic Chemistry, 1988 , vol. 53, # 6 p. 1285 - 1288

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Citation Number: 39

Abstract

Introduction of 8-functional alkyl and alkenyl groups to the adamantane bridgehead was carried out by radical-mediated reactions of 1-adamantyl bromide and iodide (la and lb) with alkenes and alkynes containing electron-withdrawing groups in the presence of tributyltin hydride and AIBN. As expected, the reactions of polybromoadamantanes 7-9 with acrylonitrile gave 1, 3-, 1, 3, 5-, and 1, 3, 5, 7-polycyanoethyl-substituted derivatives; yield ...