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Mass spectra of new heterocycles: XIII. Fragmentation of 2-(prop-1-en-1-yl)-4,5-dihydro-1,3-thiazoles under electron impact and chemical ionization

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Abstract

Fragmentation of 2-(prop-1-en-1-yl)-4,5-dihydro-1,3-thiazoles synthesized from alkoxyallenes or propargylbenzene, isothiocyanates, and benzyl, allyl, or propargyl bromide has been studied under electron impact (70 eV) and chemical ionization (with methane as reactant gas). All compounds under electron impact give rise to stable molecular ions whose decomposition involves concurrent dihydrothiazole ring cleavage and elimination of substituents. The fragmentation pattern is largely determined by the nature of the substituent on C5. Chemical ionization of 4,5-dihydro-1,3-thiazole derivatives is typically accompanied by protonation and electrophilic addition with subsequent elimination of nitrile molecule. No substituent effect on the fragmentation pattern under chemical ionization has been revealed. Unlike electron impact and chemical ionization, the most abundant ion in the MALDI mass spectrum of 2-[(Z)-1-butoxyprop-1-en-1-yl]-4,4-dimethyl-5-phenyl-4,5-dihydro-1,3-thiazole is [M — H]+.

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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, N. A. Nedolya, O. A. Tarasova & E. R. Sanzheeva

Authors
  1. L. V. Klyba
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  2. N. A. Nedolya
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  3. O. A. Tarasova
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  4. E. R. Sanzheeva
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Correspondence to N. A. Nedolya.

Additional information

Original Russian Text © L.V. Klyba, N.A. Nedolya, O.A. Tarasova, E.R. Sanzheeva, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 4, pp. 558–568.

For communication XII, see [1].

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Klyba, L.V., Nedolya, N.A., Tarasova, O.A. et al. Mass spectra of new heterocycles: XIII. Fragmentation of 2-(prop-1-en-1-yl)-4,5-dihydro-1,3-thiazoles under electron impact and chemical ionization. Russ J Org Chem 51, 541–551 (2015). https://doi.org/10.1134/S1070428015040144

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  • DOI: https://doi.org/10.1134/S1070428015040144

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