Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
The Photolysis of Ethyl Chloroformate in Hydrocarbons
Chyongjin PacShigeru Tsutsumi
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1965 Volume 38 Issue 11 Pages 1916-1921

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Abstract

The photolysis of ECF in cyclohexane, cyclohexene, oct-1-ene, and benzene has been carried out. It has been concluded that carbon-chlorine bond breaking has occurred to give ethoxycarbonyl radicals in a selective manner. The reactions of the radical in hydrocarbons have been qualitatively discussed, and it has been suggested that the radical had a life long enough to associate with a cyclohexyl radical in a solvent cage, but not a life long enough to dimerize and be added to carbon-carbon double bonds with less decomposition. Thus, cyclohexane, cyclohexene, oct-1-ene, and benzene were carboxylated. No chain reactions were observed in light- and dibenzoyl peroxide-induced reactions of ECF in hydrocarbons ; i. e., ECF was unreactive to alkyl radicals and radicals bearing an ethoxycarbonyl group on their α-carbon. The photolysis of ECF supplies a convenient method for the generation of ethoxycarbonyl radicals.

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