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Highly unsaturated trifluoromethanesulfonamide derivatives

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Abstract

Reactions of N-propargyltriflamide TfNHCH2C≡CH (Tf = CF3SO2) with allyl bromide or propargyl bromide in DMSO afforded highly unsaturated triflamide derivatives: N-allyl-N-propargyltriflamide TfN·(CH2CH=CH2)(CH2C≡CH), N-allenyl-N-allyltriflamide TfN(CH2CH=CH2)(CH=C=CH2), and N-allenyl-N-propargyltriflamide TfN(CH=C=CH2)(CH2C≡CH). By the reaction of triflamide with propargyl bromide in DMSO N,N-dipropargyltriflamide TfN(CH2C≡CH)2 was obtained, which under the treatment with t-BuOK in DMSO underwent isomerization giving an equilibrium mixture with N-allenyl-N-propargyltriflamide TfN (CH2C≡CH)(CH=C=CH2) in a ratio 85: 15.

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Authors and Affiliations

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

    B. A. Shainyan & Yu. S. Danilevich

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  1. B. A. Shainyan
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  2. Yu. S. Danilevich
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Correspondence to B. A. Shainyan.

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Original Russian Text © B.A. Shainyan, Yu.S. Danilevich, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 5, pp. 623–626.

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Shainyan, B.A., Danilevich, Y.S. Highly unsaturated trifluoromethanesulfonamide derivatives. Russ J Org Chem 51, 601–604 (2015). https://doi.org/10.1134/S1070428015050012

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  • DOI: https://doi.org/10.1134/S1070428015050012

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