Abstract
Fragmentation patterns of 5-methylsulfanyl-1-vinyl-1H-pyrrol-2-amines under electron impact (70 eV) and chemical ionization (methane as reactant gas) were studied for the first time. The electron impact mass spectra of all the examined compounds contained a strong peak of molecular ion which decomposed along four pathways. Two pathways involved cleavage of the C-S bonds with elimination of methyl (major) and MeS radicals (minor), and the two others, decomposition of the pyrrole ring. The chemical ionization mass spectra displayed strong molecular, [M + H]+, and odd-electron [M + H − SMe]+ ion peaks. N,N-Dimethyl-5-methylsulfanyl-4-phenyl-1-vinyl-1H-pyrrol-2-amine under chemical ionization with methane as reactant gas characteristically decomposed with formation of [M − C4H9N]+ as the only fragment ion.
Article PDF
Similar content being viewed by others
References
Klyba, L.V., Nedolya, N.A., Tarasova, O.A., and Sanzheeva, E.R., Russ. J. Org. Chem., 2013, vol. 49, p. 384.
Sundberg, R.J., Comprehensive Heterocyclic Chemistry, Katritzky, A.R. and Rees, C.W., Eds., Oxford: Pergamon, 1984, vol. 4, p. 313; Smith K.M., Comprehensive Heterocyclic Chemistry, Katritzky, A.R. and Rees, C.W., Eds., Oxford: Pergamon, 1984, vol. 4, p. 377; Gribble, G.W., Comprehensive Heterocyclic Chemistry II, Katritzky, A.R., Rees, C.W., and Scriven, E.F.V., Eds., Oxford: Pergamon, 1996, vol. 2, p. 207; d’Ischia, M., Napolitano, A., and Pezzella, A., Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Eds., Amsterdam: Elsevier, 2008, vol. 3, p. 353.
Trofimov, B.A. and Nedolya, N.A., Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Eds., Amsterdam: Elsevier, 2008, vol. 3, p. 45; DuBois, C.J., Jr. and McCarley, R.L., J. Electroanal. Chem., 1998, vol. 454, p. 99; Varlamov, A.V., Borisova, T.N., Voskressensky, L.G., Brook, A.A., and Chernyshev, A.I., Arkivoc, 2000, part (ii), p. 147; Wang, W., Yu, D., and Tian, F., Synth. Met., 2008, vol. 158, p. 717; Trofimov, B.A., Ivanov, A.V., Skital’tseva, E.V., Vasil’tsov, A.M., Ushakov, I.A., Petrushenko, K.B., and Mikhaleva, A.I., Synthesis, 2009, p. 3603; Schmidt, E.Yu., Ushakov, I.A., Zorina, N.V., Mikhaleva, A.I., and Trofimov, B.A., Mendeleev Commun., 2011, vol. 21, p. 36; Belyaeva, K.V., Andriyankova, L.V., Nikitina, L.P., Ivanov, A.V., Afonin, A.V., Ushakov, I.A., Mal’kina, A.G., Mikhaleva, A.I., and Trofimov, B.A., Synthesis, 2011, p. 2843; Verma, A.K., Joshi, M., and Singh, V.P., Org. Lett., 2011, vol. 13, p. 1630.
Lebedev, A.Y., Izmer, V.V., Kazyul’kin, D.N., Beletskaya, I.P., and Voskoboynikov, A.Z., Org. Lett., 2002, vol. 4, p. 623; Katritzky, A.R., Maimait, R., Xu, Y.-J., and Gyoung, Y.S., J. Org. Chem., 2002, vol. 67, p. 8230; Pinho e Melo, T.M.V.D., Soares, M.I.L., Rocha Gonsalves, A.M.d’A., Paixão, J.A., Beja, A.M., and Silva, M.R., J. Org. Chem., 2005, vol. 70, p. 6629; Movassaghi, M. and Ondrus, A.E., J. Org. Chem., 2005, vol. 70, p. 8638; Taillefer, M., Ouali, A., Renard, B., and Spindler, J.-F., Chem. Eur. J., 2006, vol. 12, p. 5301; Liao, Q., Wang, Y., Zhang, L., and Xi, C., J. Org. Chem., 2009, vol. 74, p. 6371.
Trofimov, B.A. and Mikhaleva, A.I., N-Vinilpirroly (N-Vinylpyrroles), Novosibirsk: Nauka, 1984; Trofimov, B.A., Pyrroles, Jones, R.A., Ed., New York: Wiley, 1992, part 2, p. 131; Trofimov, B.A., Mikhaleva, A.I., Shmidt, E.Yu., and Sobenina, L.N., Khimiya pirrola. Novye stranitsy (The Chemistry of Pyrrole. New Pages), Tolstikov, G.A., Ed., Novosibirsk: Nauka, 2012.
Mikhaleva, A.I., Shmidt, E.Yu., Ivanov, A.V., Vasil’tsov, A.M., Senotrusova, E.Yu., and Protsuk, N.I., Russ. J. Org. Chem., 2007, vol. 43, p. 228; Trofimov, B.A., Mikhaleva, A.I., Schmidt, E.Yu., and Sobenina, L.N., Adv. Heterocycl. Chem., 2010, vol. 99, p. 209; Vasil’tsov, A.M., Ivanov, A.V., Mikhaleva, A.I., and Trofimov, B.A., Tetrahedron Lett., 2010, vol. 51, p. 1690.
Nedolya, N.A., Ph.D. Thesis of Utrecht University, Utrecht, The Netherlands, 1999; Brandsma, L., Nedolya, N.A., Tarasova, O.A., and Trofimov, B.A., Khim. Geterotsikl. Soedin., 2000, p. 1443; Brandsma, L., Eur. J. Org. Chem., 2001, p. 4569; Brandsma, L. and Nedolya, N.A., Synthesis, 2004, p. 735; Nedolya, N.A., Khim. Geterotsikl. Soedin., 2008, p. 1443.
Nedolya, N.A., Brandsma, L., and Tolmachev, S.V., Russ. J. Org. Chem., 2002, vol. 38, p. 907; Nedolya, N.A., Brandsma, L., Tarasova, O.A., Albanov, A.I., and Trofimov, B.A., Russ. J. Org. Chem., 2011, vol. 47, p. 659.
Nedolya, N.A., Tarasova, O.A., Albanov, A.I., and Trofimov, B.A., Tetrahedron Lett., 2010, vol. 51, p. 5316; Tarasova, O.A., Nedolya, N.A., Albanov, A.I., and Trofimov, B.A., Russ. J. Org. Chem., 2010, vol. 46, p. 773.
Klyba, L.V., Bochkarev, V.N., Brandsma, L., Tarasova, O.A., Vvedenskii, V.Yu., Nedolya, N.A., and Trofimov, B.A., Russ. J. Gen. Chem., 1999, vol. 69, p. 1801; Klyba, L.V., Bochkarev, V.N., Brandsma, L., Nedolya, N.A., and Trofimov, B.A., Russ. J. Gen. Chem., 1999, vol. 69, p. 1805; Klyba, L.V., Bochkarev, V.N., Brandsma, L., Tarasova, O.A., Nedolya, N.A., and Trofimov, B.A., Izv. Akad. Nauk, Ser. Khim., 2000, p. 1560; Klyba, L.V., Bochkarev, V.N., Brandsma, L., Nedolya, N.A., and Trofimov, B.A., Izv. Akad. Nauk, Ser. Khim., 2001, p. 2282; Klyba, L.V., Nedolya, N.A., Brandsma, L., and Schlyakhtina, N.I., Arkivoc, 2001, part (ix), p. 117; Klyba, L.V., Tarasova, O.A., Brandsma, L., Nedolya, N.A., and Petrushenko, K.B., Russ. J. Org. Chem., 2006, vol. 42, p. 1003; Klyba, L.V., Nedolya, N.A., Tarasova, O.A., Zhanchipova, E.R., and Volostnykh, O.G., Russ. J. Org. Chem., 2009, vol. 45, p. 596; Klyba, L.V., Nedolya, N.A., Shlyakhtina, N.I., and Zhanchipova, E.R., Russ. J. Org. Chem., 2005, vol. 41, p. 1544; Klyba, L.V., Nedolya, N.A., and Zhanchipova, E.R., Russ. J. Org. Chem., 2008, vol. 44, p. 133; Klyba, L.V., Nedolya, N.A., Tarasova, O.A., and Zhanchipova, E.R., Russ. J. Org. Chem., 2009, vol. 45, p. 292; Klyba, L.V., Nedolya, N.A., Tarasova, O.A., Zhanchipova, E.R., and Volostnykh, O.G., Russ. J. Org. Chem., 2010, vol. 46, p. 218; Klyba, L.V., Nedolya, N.A., Tarasova, O.A., Zhanchipova, E.R., and Volostnykh, O.G., Russ. J. Org. Chem., 2010, vol. 46, p. 1038.
Nedolya, N.A., Brandsma, L., and Trofimov, B.A., Synthesis, 2013, vol. 45, p. 93.
Tarasova, O.A., Nedolya, N.A., Brandsma, L., and Albanov, A.I., Tetrahedron Lett., 2004, vol. 45, p. 5881; Nedolya, N.A., Tarasova, O.A., Volostnykh, O.G., Albanov, A.I., Klyba, L.V., and Trofimov, B.A., Synthesis, 2011, p. 2192.
Tarasova, O.A., Nedolya, N.A., Vvedensky, V.Yu., Brandsma, L., and Trofimov, B.A., Tetrahedron Lett., 1997, vol. 38, p. 7241.
Nedolya, N.A., Brandsma, L., Tarasova, O.A., Verkruijsse, H.D., and Trofimov, B.A., Tetrahedron Lett., 1998, vol. 39, p. 2409.
Brandsma, L., Nedolya, N.A., and Tolmachev, S.V., Khim. Geterotsikl. Soedin., 2002, p. 60.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © L.V. Klyba, N.A. Nedolya, O.A. Tarasova, E.R. Sanzheeva, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 1, pp. 43–51.
For communication XI, see [1].
Rights and permissions
About this article
Cite this article
Klyba, L.V., Nedolya, N.A., Tarasova, O.A. et al. Mass spectra of new heterocycles: XII. Main fragmentation pathways of the molecular ions of 5-methylsulfanyl-1-vinyl-1H-pyrrol-2-amines under electron impact and chemical ionization. Russ J Org Chem 50, 35–44 (2014). https://doi.org/10.1134/S1070428014010072
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428014010072