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1,3‐Elimination in 2‐( Tert ‐alkyl)adamantan‐2‐ols: An easy synthesis of bridgehead‐substituted 2,4‐dehydroadamantanes
Author(s) -
Lomas John S.
Publication year - 1996
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199608)9:8<588::aid-poc824>3.0.co;2-v
Subject(s) - chemistry , substituent , cyclopropane , alkyl , bromide , pyridine , medicinal chemistry , tricyclic , ring (chemistry) , organic chemistry
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 2,4‐dehydroadamantanes bearing the tert ‐alkyl substituent on the cyclopropane system.