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The Mechanism of Acylcarbene Insertion into OH Bonds—Direct Observation of the Enol of a Carboxylic Acid Ester in Aqueous Solution
Author(s) -
Chiang Yvonne,
Kresge A. Jerry,
Pruszynski Przemyslaw,
Schepp Norman P.,
Wirz Jakob
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199113661
Subject(s) - enol , tautomer , carbene , chemistry , aqueous solution , carboxylic acid , medicinal chemistry , photodissociation , reaction mechanism , photochemistry , stereochemistry , polymer chemistry , organic chemistry , catalysis
The addition of water to the acyl carbene function as a whole is a better description for the reaction (a) than the insertion of carbene 1 into the OH bond of water. The enol tautomer 2 of methyl mandelate was shown to be an intermediate. If the photolysis is conducted in 18 O‐enriched water, 3 is marked exclusively at the α‐hydroxyl group.