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The synthesis of substituted adamantanes from dehydroadamantane

โœ Scribed by A.C. Udding; J. Strating; Hans Wynberg

Book ID
104249545
Publisher
Elsevier Science
Year
1968
Tongue
French
Weight
297 KB
Volume
9
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

A large number of bridgehead substituted adamantanes are known (1). The number of secondary substituted adamantanes however is limited since their synthesis could formerly only be achieved by low yield ring-closure reactions (1).

Recently some high yield ring-closure reactions for the preparation of polyfunctional secondary substituted adanantanes have been described (2,3).

In addition the reported syntheses of a 1,2-substituted adamantane (4) and of adamantanone (5) offer a good route to 2-substituted adamantanes.

Dehydroadauaneane (tetracyclo[3,3,1,13*7,02V4 ]decane) I, prepared in our laboratory (6), proved to be a very useful source for the synthesis of 2-substituted and 2,4_disubstituted adamantanes (II and III).

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When 2-(tert-alkyl)adamantan-2-ols (where the substituent is bi-or tricyclic) are thermolysed or the corresponding bromide is refluxed in pyridine, an unusual 1,3-elimination occurs, leading to 2,4dehydroadamantanes bearing the tert-alkyl substituent on the cyclopropane system.