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Mass spectra of new heterocycles: XV. Fragmentation of 1-substituted 3-alkoxy-2-(propargylsulfanyl)- and 3-alkoxy-2-(allenylsulfanyl)-1H-pyrroles under electron impact

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Abstract

The electron impact mass spectra of 1-R-substituted 3-alkoxy-2-(propargylsulfanyl)- and 3-alkoxy-2-(allenylsulfanyl)-1H-pyrroles (R = Me, i-Pr, s-Bu, Ph) have been studied for the first time. These compounds give rise to stable molecular ions whose primary fragmentation follows three competing pathways: cleavage of the C–O bonds with expulsion of alkyl radical, cleavage of the C–S bonds with formation of [M–C3H3]+ ions, and cleavage of the C–N bonds with synchronous hydrogen transfer to give odd-electron [M–CnH2n]+ · ion. The main fragmentation pathway of 2-(propargylsulfanyl) derivatives is cleavage of the C–S bond with formation of [M–C3H3]+ ion.

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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

    L. V. Klyba, O. A. Tarasova & N. A. Nedolya

Authors
  1. L. V. Klyba
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  2. O. A. Tarasova
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  3. N. A. Nedolya
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Correspondence to L. V. Klyba.

Additional information

Original Russian Text © L.V. Klyba, O.A. Tarasova, N.A. Nedolya, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 12, pp. 1782–1787.

For communication XIV, see [1].

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Klyba, L.V., Tarasova, O.A. & Nedolya, N.A. Mass spectra of new heterocycles: XV. Fragmentation of 1-substituted 3-alkoxy-2-(propargylsulfanyl)- and 3-alkoxy-2-(allenylsulfanyl)-1H-pyrroles under electron impact. Russ J Org Chem 52, 1773–1778 (2016). https://doi.org/10.1134/S1070428016120101

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  • DOI: https://doi.org/10.1134/S1070428016120101

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