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Condensation products of mono-and dibromo-substituted methyl vinyl sulfones with CH-acids enolates

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Bromomethyl (E)-2-phenylethenyl and bromomethyl (Z)-1-bromo-2-phenylethenyl sulfones undergo condensation with enolates generated from malononitrile, dimethyl malonate, methyl and ethyl acetoacetate using NaH in THF to give tetrahydrothiophene S,S-dioxides. Methyl (E)-1-bromo-2-phenylethenyl and methyl (E)-2-bromo-2-phenylethenyl sulfones react with sodium malononitrile to give 2-[2-(methylsulfonyl)-1-phenylethylidene]malononitrile. The bromomethyl-(E)-2-bromo-2-phenyl ethenyl sulfone reacts with sodium malononitrile to give 2-[2-(bromomethylsulfonyl)-1-phenylethylidene]malononitrile exclusively.

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Authors and Affiliations

  1. N. P. Ogarev Mordovian State University, Saransk, 430000, Russia

    V. A. Vasin & I. Yu. Bolusheva

  2. St. Petersburg State University, St. Petersburg, 198504, Russia

    V. V. Razin

Authors
  1. V. A. Vasin
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  2. I. Yu. Bolusheva
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  3. V. V. Razin
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Correspondence to V. A. Vasin.

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Dedicated to Professor A. A. Potekhin’s memory.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 539–551, April, 2008.

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Vasin, V.A., Bolusheva, I.Y. & Razin, V.V. Condensation products of mono-and dibromo-substituted methyl vinyl sulfones with CH-acids enolates. Chem Heterocycl Comp 44, 419–429 (2008). https://doi.org/10.1007/s10593-008-0058-9

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  • DOI: https://doi.org/10.1007/s10593-008-0058-9

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