Facial selectivity in the addition of nucleophiles to the radical cations of substituted 2-methyleneadamantanes

…, K Janz, G Jocys, A Pincock, J Pincock

Index: Swansburg; Janz; Jocys; Pincock Canadian Journal of Chemistry, 1998 , vol. 76, # 1 p. 35 - 47

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Citation Number: 5

Abstract

The diphenylmethylenecyclohexane, 2, and the substituted 2-methyleneadamantanes, 3-7, have been prepared. The radical cation of each was generated by photochemical oxidation using 1, 4-dicyanobenzene as the sensitizer, and their reactivity was examined in methanol- acetonitrile mixtures with added tetraethylammonium cyanide. Although compound 2 reacted only by tautomerization, the other compounds all gave addition products. For the ...