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Electrophilic and Nucleophilic Addition Reactions of α,β-Unsaturated Diphenylphosphoryl Compounds

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Abstract

Procedures were developed for the synthesis of diphenyl(prop-1-en-1-yl)phosphine oxide and cyclohex-1-en-1-yl(diphenyl)phosphine oxide by alkaline hydrolysis of triphenyl(prop-1-en-1-yl)phosphonium bromide and cyclohex-1-en-1-yl(triphenyl)phosphonim bromide, respectively. The bromination of diphenyl(vinyl)phosphine oxide, diphenyl(prop-1-en-1-yl)phosphine oxide, and cyclohex-1-en-1-yl(diphenyl)phosphine oxide with excess bromine gave the corresponding 1,2-dibromo derivatives. Dehydrobromination of 1,2-dibromoethyl(diphenyl)phosphine oxide and 1,2-dibromopropyl(diphenyl)phosphine oxide with sodium hydroxide afforded 1-bromoethenyl(diphenyl)phosphine oxide and 1-bromoprop-1-en-1-yl(diphenyl)phosphine oxide. Addition of bromine and methanol to 1-bromoethenyl(diphenyl)phosphine oxide and 1-bromoprop-1-en-1-yl-(diphenyl)phosphine oxide was studied.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Scientific Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of Armenia, Yerevan, 0014, Armenia

    M. Zh. Ovakimyan, G. Ts. Gasparyan, A. S. Poghosyan, A. S. Bichakhchyan & L. V. Derdzyan

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  1. M. Zh. Ovakimyan
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  2. G. Ts. Gasparyan
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  3. A. S. Poghosyan
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  4. A. S. Bichakhchyan
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  5. L. V. Derdzyan
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Correspondence to A. S. Bichakhchyan.

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The authors declare the absence of conflict of interest.

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Russian Text © The Author(s), 2020, published in Zhurnal Organicheskoi Khimii, 2020, Vol. 56, No. 1, pp. 112–117.

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Ovakimyan, M.Z., Gasparyan, G.T., Poghosyan, A.S. et al. Electrophilic and Nucleophilic Addition Reactions of α,β-Unsaturated Diphenylphosphoryl Compounds. Russ J Org Chem 56, 90–94 (2020). https://doi.org/10.1134/S1070428020010157

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  • DOI: https://doi.org/10.1134/S1070428020010157

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