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1,3-Elimination in 2-(Tert-alkyl)adamantan-2-ols: An easy synthesis of bridgehead-substituted 2,4-dehydroadamantanes

✍ Scribed by John S. Lomas

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 315 KB
Volume: 9
Category: Article
ISSN: 0894-3230
DOI: 10.1002/(sici)1099-1395(199608)9:8<588::aid-poc824>3.0.co;2-v

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✦ Synopsis

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.

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