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Unknown Camphor: Regioselective Rearrangement under Acylation in a CF 3 SO 3 H/(CF 3 CO) 2 O System
Author(s) -
Kovalev Vladimir,
Shokova Elvira,
Chertkov Vyacheslav,
Tafeenko Victor
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201501581
Subject(s) - camphor , chemistry , regioselectivity , acylation , moiety , medicinal chemistry , heptane , aryl , bicyclic molecule , alkyl , stereochemistry , organic chemistry , catalysis
The utility of camphor in the chemical sciences is vast and well documented, yet the creation of camphor‐derived potentially useful bicyclo[2.2.1]heptane scaffolds still remains one of the great challenges of synthetic organic chemistry. Herein, we show that CF 3 SO 3 H/(CF 3 CO) 2 O‐mediated acylation of camphor with benzoic acids is accompanied by a cascade of alkyl and hydride shifts and opens access to a new type of polyfunctional isoborneol. In case of salicylic acids, camphor feels the presence of the ortho ‐hydroxy group in the aryl moiety, the influence of which provokes cleavage of the bicycloheptane skeleton to lead to monocyclic carvenone.