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The photodecomposition and photoracemization of methyl (+)-O-methylmandelate

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
31
Issue
16
Identifiers
DOI: 10.1016/0040-4020(75)87030-x

Abstract

Abstract Irradiation at 254 nm of the bichromorphoric molecule methyl (+)-O-methylmandelate ((+)- 3) in methanol has been found to lead to photodecomposition and photoracemization. The major monomeric product isolated, methyl phenylacetate ( 1b), is shown to arise by a mechanism totally different from that responsible for racemization. The high efficiency of the direct irradiation, the very short singlet lifetime of 3 ( ca 1 nsec), and the inability to sensitize the formation of 1b with acetone triplets implicate the singlet state of 3 as the reactive species. Mechanistic models to account for the products are discussed.

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