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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 2
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Original Articles

New Synthesis of Mono-Halogenated Adamantanes

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Pages 147-151 | Received 20 Feb 1973, Published online: 06 Dec 2006
 

Abstract

A variety of direct halogenations on the adamantane skeleton have been reported. For example, bromination of adamantane with bromine, which is considered to proceed through an ionic mechanism, gives high yield of 1-broinoadamsntane. In contrast to the ionic bromination of adamantane, chlorinations are much less selective2,3,4,5. Photochloroadamantane of adamantane gives l-chloroadamntane and 2-chloroadamantane. Chlorination with t-butyl chloride in the presence of A1C13 gives rise to a mixture of 1-chloroadamantane and 1,3-dichloroadamantane.

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