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Title: The reactions of 3‐Butyl‐1,2‐diphenylphosphindole with dimethyl acetylenedicarboxylate
Authors: Alan N. Hughes
Kitti Amornraksa
Siriporn Phisithkul
Vichai Reutrakul
Lakehead University
Mahidol University
Keywords: Chemistry
Issue Date: 1-Jan-1976
Citation: Journal of Heterocyclic Chemistry. Vol.13, No.1 (1976), 65-72
Abstract: Unlike 1,2,5‐triphenylphosphole, 3‐butyl‐1,2‐diphenylphosphindole reacts smoothly with two molecules of dimethyl acetylenedicarboxylate to give the phosphindole oxide, a yellow adduct and a colourless adduct. The case of the reaction is taken to indicate less lone pair interaction with the π‐system in phosphindoles than in phospholes. The yellow adduct is shown to be a phosphindolium cyclopentadienylide, i.e. an adduct of the phosphindole and two molecules of the ester less one oxygen atom. The colourless adduct is shown to be a 1:2:1 adduct of the phosphindole, the ester and water and has a benzodihydrophosphonin structure. Mechanisms for the formation of both adducts are proposed. Adducts of this general type were previously unknown in organophosphorus chemistry. Copyright © 1976 Journal of Heterocyclic Chemistry
ISSN: 19435193
Appears in Collections:Scopus 1969-1990

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