Issue 0, 1974

Bridgehead reactivity in protoadamantane. Ionic bromination

Abstract

In agreement with computer molecular mechanics calculations, the preponderant product of bromination of protoadamantane (tricyclo[4.3.1.03,8]decane) is the 6-bromo-derivative. The structure elucidation is based on the finding that 6-methylprotoadamantane is significantly less reactive in bromination than is protoadamantane. 6-Bromoprotoadamantane reacts readily in several nucleophilic substitution reactions.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1974, 2475-2479

Bridgehead reactivity in protoadamantane. Ionic bromination

A. Karim and M. A. Mckervey, J. Chem. Soc., Perkin Trans. 1, 1974, 2475 DOI: 10.1039/P19740002475

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