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Efficient synthetic methods for unsaturated 3,4,5-trimethoxybenzyl sulfides and ethers

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Abstract

Convenient and efficient procedures were developed for preparation of 3,4,5-trimethoxybenzyl sulfides and ethers containing vinyl, allyl, and propargyl groups proceeding from 3,4,5-trimethoxybenzyl alcohol, elemental sulfur, and thiourea in basic and basic-reductive systems (hydrazine hydrate‒KОН‒DMF, NaBH4‒EtOH, KОН‒DMSO). The effective method of the synthesis of 1,1'-[disulfandiylbis(methylene)]bis-(3,4,5-trimethoxybenzene) consists in the reduction of the elemental sulfur to disulfide anion with hydrazine hydrate in the presence of KОН followed by the reaction with 3,4,5-trimethoxybenzyl chloride under the conditions of phase-transfer catalysis or in DMF.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    V. A. Potapov, V. A. Panov, M. V. Musalov, S. A. Zhivet’eva, M. V. Musalova, A. G. Khabibulina & S. V. Amosova

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  1. V. A. Potapov
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  2. V. A. Panov
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  3. M. V. Musalov
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  4. S. A. Zhivet’eva
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  5. M. V. Musalova
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  6. A. G. Khabibulina
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  7. S. V. Amosova
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Corresponding author

Correspondence to S. V. Amosova.

Additional information

Original Russian Text © V.A. Potapov, V.A. Panov, M.V. Musalov, S.A. Zhivet’eva, M.V. Musalova, A.G. Khabibulina, S.V. Amosova, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 11, pp. 1579–1583.

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Potapov, V.A., Panov, V.A., Musalov, M.V. et al. Efficient synthetic methods for unsaturated 3,4,5-trimethoxybenzyl sulfides and ethers. Russ J Org Chem 52, 1571–1575 (2016). https://doi.org/10.1134/S107042801611004X

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  • DOI: https://doi.org/10.1134/S107042801611004X

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