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Functional sulfur-containing compounds. 10. Alkylation of ch-acids with 2-[(organylthio)methyl]oxirans

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Abstract

In the reaction of 2-[(organylthio)methyl]oxirans (I) with malonic, acetoacetic and cyanoacetic esters mixtures of 4- and 5-[(organylthio)methyl]-3-(methoxy-carbonyl-, acetyl-, cyano-)-4, 5-dihydro-2(3H)-furanones (II)-(VII) are formed. The ratio of the isomers depends on the nature of the CH-acid. The reaction of 2-[(ethylthio)methyl]oxiran (Ia) with bis(butylsulfonyl)methane leads to a mixture of 3-(ethylthio)-1-[bis(butylsulfonyl)methyl]-propan-2-ol (XIa) and 3-(ethylthio)-2-[bis(butylsulfonyl)methyl]propan-1-ol (XIIa) in a 1∶1 ratio. In the reaction of epoxides (I) with acetylacetone 4-[(organylthio)methyl]-2-methyl-2-acetonyl-1, 3-dioxolanes (XIII) are formed.

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Literature cited

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    V. E. Kalugin & V. P. Litvinov

Authors
  1. V. E. Kalugin
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  2. V. P. Litvinov
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Additional information

For previous communication, see [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2829–2832, December, 1991.

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Kalugin, V.E., Litvinov, V.P. Functional sulfur-containing compounds. 10. Alkylation of ch-acids with 2-[(organylthio)methyl]oxirans. Russ Chem Bull 40, 2467–2469 (1991). https://doi.org/10.1007/BF00959724

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  • DOI: https://doi.org/10.1007/BF00959724

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