Organoselenium chemistry. 13. Reaction of areneselenenyl chlorides and alkenes. An example of nucleophilic displacement at bivalent selenium

GH Schmid, DG Garratt

Index: Schmid, George H.; Garratt, Dennis G. Journal of Organic Chemistry, 1983 , vol. 48, p. 4169 - 4172

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Citation Number: 30

Abstract

The effect of substituents in the phenyl ring of both the electrophile and the alkene has been studied in the reaction of areneselenenyl chlorides and (E)-and (2)-1-phenylpropenes. Electron-donating groups in both phenyl rings enhance the rate of reaction. Viewing this reaction as a nucleophilic displacement at bivalent selenium leads to a model that allows the possibility of reaction by a continuum of mechanisms. These mechanisms differ only in ...