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Synthesis of 9-substituted homoadamantanes

✍ Scribed by Zdenko Majerski; Zdenko Hameršak

Book ID: 104237306
Publisher: Elsevier Science
Year: 1978
Tongue: French
Weight: 150 KB
Volume: 19
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)85619-7

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✦ Synopsis

Although the homoadamantane system has been extensively studied, 192 no g-substituted homoadamantane derivative has been previously prepared. g-substituted homoadamantanes are interesting compounds which resemble structurally the 2-substituted adamantanes, but which should rearrange more readily.

In this work we report a convenient, 79% overall yield synthesis of 9-homoadamantanone (2) from lo-homoprotoadamantan-4-one

(2, tricycle 4.3.2.0 [ 398 3 undecan-4-one). This ketone is readily available by thermolysis of 1-homoadamantyl hypoiodite (prepared in situ from 1-homoadamantanol, 1) followed by the base promoted intramolecular cyclization of the resulting iodoketone. 3

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