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Nucleophilic Addition of Enols and Enamines to α,β‐Unsaturated Acyl Azoliums: Mechanistic Studies
Author(s) -
Samanta Ramesh C.,
Maji Biplab,
De Sarkar Suman,
Bergander Klaus,
Fröhlich Roland,
MückLichtenfeld Christian,
Mayr Herbert,
Studer Armido
Publication year - 2012
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/anie.201109042
Subject(s) - deprotonation , reactivity (psychology) , nucleophile , chemistry , nucleophilic addition , salt (chemistry) , sigmatropic reaction , double bond , stereochemistry , medicinal chemistry , computational chemistry , organic chemistry , catalysis , medicine , ion , alternative medicine , pathology
1,4 but not 1,2! The reactivity of 1 towards different nucleophiles (deprotonated β‐diketones, enamines, and malonodinitrile) was investigated by NMR and kinetic experiments. These investigations proved that CC bond formation occurs by a Michael‐type 1,4‐addition and not by a 1,2‐addition and subsequent [3,3]‐sigmatropic rearrangement. The first X‐ray structure of an α,β‐unsaturated acyl azolium salt ( 1 ) is also presented.
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