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Direct Synthesis of N ‐Arylquinone Imine Acetals and Quinol Imines from Acetals
Author(s) -
Carreño M. Carmen,
Cuerva Juan M.,
Ribagorda María,
Echavarren Antonio M.
Publication year - 1999
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(19990517)38:10<1449::aid-anie1449>3.0.co;2-m
Subject(s) - imine , chemistry , aldehyde , ketone , nucleophile , quinone , acetal , catalysis , organic chemistry , medicinal chemistry
In the absence of any added acidic catalyst quinone acetals as well as simple ketone and aldehyde acetals react with a variety of substituted anilines to form imines [Eq. (a)]. Contrary to what is expected from arguments based on their nucleophilicity, the most reactive anilines are those bearing electron‐withdrawing groups.