Publication: The reactions of 3‐Butyl‐1,2‐diphenylphosphindole with dimethyl acetylenedicarboxylate
1
Issued Date
1976-01-01
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ISSN
19435193
0022152X
0022152X
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2-s2.0-11544274519
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Mahidol University
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SCOPUS
Bibliographic Citation
Journal of Heterocyclic Chemistry. Vol.13, No.1 (1976), 65-72
Suggested Citation
Alan N. Hughes, Kitti Amornraksa, Siriporn Phisithkul, Vichai Reutrakul The reactions of 3‐Butyl‐1,2‐diphenylphosphindole with dimethyl acetylenedicarboxylate. Journal of Heterocyclic Chemistry. Vol.13, No.1 (1976), 65-72. doi:10.1002/jhet.5570130112 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/10858
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Title
The reactions of 3‐Butyl‐1,2‐diphenylphosphindole with dimethyl acetylenedicarboxylate
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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