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Selectivity in photolysis of benzyl acetate and benzyl hexanoate upon cyclodextrin complexation

Paper ID Volume ID Publish Year Pages File Format Full-Text
28574 44081 2006 10 PDF Available
Title
Selectivity in photolysis of benzyl acetate and benzyl hexanoate upon cyclodextrin complexation
Abstract

Irradiation of benzyl acetate (1) and benzyl hexanoate (2) in methanol yields products from both heterolytic and homolytic pathways. However, in presence of cyclodextrin, photolysis of 1 in aqueous solution and in solid state produces benzyl alcohol as the predominant product and this is attributed to the stabilization of benzylcarbonium ion by secondary hydroxyl groups present at the rim of the cyclodextrin cavity. However, photolysis of 2, in presence of cyclodextrin, produces hexylbenzene as the predominant product via a homolytic pathway and the change in selectivity is explained by the coinclusion of spacer group inside the cyclodextrin cavity.

Keywords
Cyclodextrin; Photolysis; Benzyl esters; Homolytic and heterolytic mechanisms
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Selectivity in photolysis of benzyl acetate and benzyl hexanoate upon cyclodextrin complexation
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 184, Issues 1–2, 15 November 2006, Pages 34–43
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
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