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A methodology for synthesis of primary o-phenylenebisphosphines and o-chlorophenylphosphines

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Abstract

On the basis of the reaction of ethynediylbisphosphonates and chloroethynylphosphonates with classical donor alka-1,3-dienes, a general strategy for synthesis of o-bisphosphanylbenzenes and o-chlorophosphanylbenzenes, which includes two consecutive steps: Diels-Alder condensation → aromatization of the carbocyclic phosphonate (bisphosphonate) formed → reduction of the phosphonate groups, was developed. Convenient procedures are devised for aromatization of phosphorus-containing cyclohexa-1,4-dienes and for reduction of o-phenylenebisphosphonates and o-clorophenylphosphonates to primary phosphines. A series of new alkylsubstituted phosphonic chlorides were prepared, and a possibility of functionalization of methylsubstituted o-phenylenebisphosphonates and o-clorophenylphosphonates by the methyl groups is demonstrated.

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology, Technical University, Moskovskii pr. 26, St. Petersburg, 190013, Russia

    S. N. Tverdomed, A. V. Dogadina & B. I. Ionin

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  1. S. N. Tverdomed
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  2. A. V. Dogadina
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  3. B. I. Ionin
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Original Russian Text © S.N. Tverdomed, A.V. Dogadina, B.I. Ionin, 2006, published in Zhurnal Obshchei Khimii, 2006, Vol. 76, No. 6, pp. 925–934.

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Tverdomed, S.N., Dogadina, A.V. & Ionin, B.I. A methodology for synthesis of primary o-phenylenebisphosphines and o-chlorophenylphosphines. Russ J Gen Chem 76, 885–894 (2006). https://doi.org/10.1134/S1070363206060089

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  • DOI: https://doi.org/10.1134/S1070363206060089

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