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The effect of fluorine as leaving group in the photolysis of 2-fluoro-1,2-diphenylethanone: Preparative and mechanistic investigation

Paper ID Volume ID Publish Year Pages File Format Full-Text
27942 44051 2008 12 PDF Available
Title
The effect of fluorine as leaving group in the photolysis of 2-fluoro-1,2-diphenylethanone: Preparative and mechanistic investigation
Abstract

Photolysis of 2-fluoro-1,2-diphenylethanone (1) in MeCN or MeOH produces mainly 2-phenylbenzofuran. In MeOH some traces of solvent addition to the benzoyl radical formed by α-cleavage were detected. In trifluoroethanol several products are due to direct α-cleavage. Only 3% of 2-phenylbenzofuran and 13% of the α-ketocation solvent adduct are formed. The triplet state of 1 observed in nanosecond experiment at low temperature has been confirmed in femtosecond experiment. The triplet is formed quite fast at 370 nm (rise time 4.5 ps in acetonitrile and 22 ps in trifluoroethanol) and is stable up to 1.9 ns (a lifetime of 20 ns has been determined by quenching experiments with naphthalene).

Keywords
Cyclization; Fluoroethanone; Benzoin; Benzofuran
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The effect of fluorine as leaving group in the photolysis of 2-fluoro-1,2-diphenylethanone: Preparative and mechanistic investigation
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 199, Issue 1, 5 September 2008, Pages 73–84
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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