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Reactions of phenylenedioxytrihalophosphoranes with arylacetylenes: XIII. Reaction of 5-tert-butyl-2,2,2-trihalo-1,3,2λ5-benzodioxaphospholes with acetylenes

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Abstract

Reactions of 5-tert-butyl-2,2,2-trichloro-, 2,2,2-tribromo-5-tert-butyl-, and 2,2-dibromo-5-tert-butyl-2-fluoro-1,3,2λ5-benzodioxaphospholes with aryl- and alkylacetylenes lead to quantitative formation of 2-halo-1,2λ5-benzoxaphosphinine 2-oxides which may be regarded as phosphorus analogs of natural heterocyclic compounds, coumarin and chromene. The major products (>70%) are 4-aryl-7-tert-butyl-2,6-dichloro-, 4-aryl-2-bromo-7-tert-butyl-, and 4-aryl-7-tert-butyl-2-fluoro-1,2λ5-benzoxaphosphinine 2-oxides. Hydrolysis of these compounds and their treatment with amines gives the corresponding 2-hydroxy and 2-amino derivatives, as well as ammonium salts. The structure of some compounds was proved by X-ray analysis.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia

    V. F. Mironov, A. V. Nemtarev, E. N. Varaksina, A. A. Shtyrlina, A. T. Gubaidullin, I. A. Litvinov & A. B. Dobrynin

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  1. V. F. Mironov
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  2. A. V. Nemtarev
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  3. E. N. Varaksina
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  4. A. A. Shtyrlina
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  5. A. T. Gubaidullin
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  6. I. A. Litvinov
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  7. A. B. Dobrynin
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Correspondence to V. F. Mironov.

Additional information

Dedicated to Full Member of the Russian Academy of Sciences O.N. Chupakhin on his 80th anniversary

Original Russian Text © V.F. Mironov, A.V. Nemtarev, E.N. Varaksina, A.A. Shtyrlina, A.T. Gubaidullin, I.A. Litvinov, A.B. Dobrynin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 6, pp. 880–902.

For communication XII, see [1].

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Mironov, V.F., Nemtarev, A.V., Varaksina, E.N. et al. Reactions of phenylenedioxytrihalophosphoranes with arylacetylenes: XIII. Reaction of 5-tert-butyl-2,2,2-trihalo-1,3,2λ5-benzodioxaphospholes with acetylenes. Russ J Org Chem 50, 864–887 (2014). https://doi.org/10.1134/S1070428014060190

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  • DOI: https://doi.org/10.1134/S1070428014060190

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