The Mechanism of Acylcarbene Insertion into OH Bonds—Direct Observation of the Enol of a Carboxylic Acid Ester in Aqueous Solution | Zendy

Chiang Yvonne | Zendy; Kresge A. Jerry | Zendy; Pruszynski Przemyslaw | Zendy; Schepp Norman P. | Zendy; Wirz Jakob | Zendy

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The Mechanism of Acylcarbene Insertion into OH 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.

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