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Reaction of 1-substituted adamantanes with bromine atoms

✍ Scribed by Gerald Jay Gleicher; John L. Jackson; Peter H. Owens; Jerry D. Unruh

Publisher: Elsevier Science
Year: 1969
Tongue: French
Weight: 203 KB
Volume: 10
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)87822-9

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✦ Synopsis

A recent investigation of hydrogen abstraction by the trichloromethyl radical from l-substituted adamantanes has been reported by us (1). It was observed that appreciable halogen abstraction by the radical occurred for 1-fluoroadamantane and l-chloroadamantane. Similar halogen abstraction from adamantanes has been also observed using other carbon radicals (2).

In order to re-examine the results of our previous study, we have repeated our experiments using bromine generated photolytically from N-bromosuccinimide as the abstracting agent.

The reactions are carried out competitively in carbon tetrachloride. Four products are obtained from adamantane.

These are, in order of elution from a 5% SE 30 gas chroinatographic column, 1-chloroadamantan8, 2-chloroadamantane, l-bromoadsmantane and 2-bromoadamantane.

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