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Reaction of trifluoromethanesulfonamide with heterodienes under oxidation conditions

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Abstract

Reactions of trifluoromethanesulfonamide with divinyl sulfone, divinyl sulfoxide, divinyl sulfide, diphenyl sulfide, vinyl allyl and diallyl ethers was investigated in the presence of oxidation system t-BuOCl + NaI. The reaction with divinyl sulfone afforded a product of 1,5-heterocyclization, 2,6-diiodo-4-[(trifluoromethyl) sulfonyl]thiomorpholine 1,1-dioxide. The same product was obtained in the reaction with divinyl sulfoxide apparently due to its preliminary oxidation to sulfone. In reactions with divinyl sulfide and unsaturated ethers only the oxidation of substrates was observed accompanied with strong tarring; the products of a reaction with trifluoromethanesulfonamide were absent. With diphenyl sulfide a product was formed resulting from the oxidation at the sulfur atom [S(II) → S(IV)], N-(diphenyl-λ4-sulfanylidene)trifluoromethanesulfonamide.

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Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, Irkutsk, 664033, Russia

    M. Yu. Moskalik, V. V. Astakhova & B. A. Shainyan

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  1. M. Yu. Moskalik
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  2. V. V. Astakhova
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  3. B. A. Shainyan
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Correspondence to M. Yu. Moskalik.

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Original English Text © M.Yu. Moskalik, V.V. Astakhova, B.A. Shainyan, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 11, pp. 1592–1596.

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Moskalik, M.Y., Astakhova, V.V. & Shainyan, B.A. Reaction of trifluoromethanesulfonamide with heterodienes under oxidation conditions. Russ J Org Chem 49, 1567–1571 (2013). https://doi.org/10.1134/S107042801311002X

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  • DOI: https://doi.org/10.1134/S107042801311002X

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