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Rate Enhancement of the Radical 1,2‐Acyloxy Shift (Surzur–Tanner Rearrangement) by Complexation with Lewis Acids
Author(s) -
Lacôte Emmanuel,
Renaud Philippe
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980904)37:16<2259::aid-anie2259>3.0.co;2-u
Subject(s) - lewis acids and bases , chemistry , radical , medicinal chemistry , alkyl , organic chemistry , catalysis
New prospects for synthetic applications are offered by the 1,2‐acyloxy shift of β ‐(acyloxy)alkyl radicals, which proceeds with high yields under Lewis acidic conditions [Eq. (1)]. With the exception of cyclizations, this is the first Lewis acid mediated acceleration of a radical rearrangement.