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Magnetic field effects on photochemical reaction III. Mechanistic study of the photodecarboxylation of arylmethyl esters in micellar solutions
Author(s) -
Tong ZhenHe,
Tung ChenHo,
Yuan LongHua
Publication year - 1991
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19910090612
Subject(s) - chemistry , photodissociation , photochemistry , micellar solutions , acetonitrile , singlet state , radical , excited state , micelle , aqueous solution , organic chemistry , physics , nuclear physics
Photolysis of benzyl phenylacetate (ACO 2 A), benzyl p ‐methylphenylacetate (BCO 2 A) and 1‐naphthyl phenylacetate (ACO 2 Np) in homogeneous and micellar solutions results in products typical of radical coupling reactions and loss of carbon dioxide. The cage effects upon direct photolysis of these esters in acetonitrile are significantly greater than zero and those in SDS or HDTBr micellar solutions are even greater. In the triplet sensitization reaction of ACO 2 Np in micellar solutions the cage effects are smaller than those obtained upon direct irradiation. However, the application of a 0.05 or 0.2 T external magnetic field in the photolysis in micellar solutions decreases the cage effects dramatically. All these results suggest that the photoextrusions of carbon dioxide from these esters proceed via radical intermediates, and upon direct photolysis the reactive states for the cleavage reaction involve both singlet and triplet excited states.