Abstract
The mass spectra of nine compounds of the perimidine series, as well as 1,3-dimethyl derivatives of 2,3-dihydroperimidine, perimidone, and thioperimidone, were obtained and are discussed. The perimidines are distinguished by their high resistance to electron impact. The initial fragmentation of their molecular ions is characterized by detachment of the substituent attached to nitrogen, as well as by detachment of a hydrogen atom from the N-methyl group. It is proposed that the intensities of the doubly charged M2+ ions be used to estimate the π-donor properties of heterocyclic compounds.
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Literature cited
N. M. Starshikov and A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 1, 96 (1980).
A. F. Pozharskii, I. S. Kashparov, V. N. Koroleva, V. I. Sokolov, and I. V. Borovlev, Summaries of Papers Presented at the First All-Union Conference on the Chemistry of Heterocyclic Compounds (Nitrogen Heterocycles) [in Russian], Chernogolovka (1973), p. 101.
E. J. Browne, Austral. J. Chem.,26, 449 (1973).
S. Lahiri, M. P. Mahajan, R. Prasad, and M. V. George, Tetrahedron,33, 3159 (1977).
T. V. Stupnikova, A. K. Sheinkman, A. F. Pozharskii, N. A. Klyuev, and É. I. Istratov, Khim. Geterotsikl. Soedin., No. 12, 1682 (1976).
R. A. Khmel'nitskii, Khim. Geterotsikl. Soedin., No. 3, 291 (1974).
R. A. Khmel'nitskii, A. N. Kost, K. K. Reddi, and V. I. Vysotskii, Zh. Org. Khim.,5, 1153 (1969).
A. F. Pozharskii, I. S. Kashparov, P. J. Holls, and V. G. Zaletov, Khim. Geterotsikl. Soedin., No. 4, 543 (1971).
A. F. Pozharskii, A. N. Suslov, N. M. Starshikov, L. N. Popova, N. A. Klyuev, and V. M. Adanin, Zh. Org. Khim.,16 (1980, in press).
Catalog of Mass Spectral Data, Am. Petroleum Inst., Research Project 44, Carnegie Inst. of Technology, Pittsburgh.
E. Stenhagen and S. Abrahamsson (eds.), Atlas of Mass Spectral Data, New York-London-Sydney-Toronto (1972).
A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 6, 723 (1977).
V. V. Dal'nikovskaya, I. V. Komissarov, A. F. Pozharskii, and I. T. Filippov, Khim.-Farm. Zh., No. 7, 85 (1978).
N. A. Klyuev, A. K. Sheinkman, R. A. Khmel'nitskii, G. A. Mal'tseva, and N. R. Kal'nitskii, Zh. Org. Khim.,33, 1079 (1977).
O. S. Anisimova, L. F. Linberg, and Yu. N. Sheinker, Mass Spectroscopy in the Study of the Metabolism of Medicinal Preparations [in Russian], Moscow (1978), p. 91.
L. S. Yang and H. Shechter, Chem. Commun., No. 19, 775 (1976).
R. Neidlein and F. Moller, Synthesis, No. 9, 685 (1978).
S.-O. Lawesson, G. Schroll, J. H. Bowie, and R. G. Cooks, Tetrahedron,24, 1875 (1968).
V. I. Vysotskii, R. A. Khmel'nitskii, and I. I. Grandberg, Izv. Timiryazevsk. Skh. Akad., No. 5, 217 (1970).
N. A. Klyuev, R. A. Khmel'nitskii, T. A. Kozik, S. B. Nikitina, and I. I. Grandberg, Zh. Org. Khim.,9, 2441 (1973).
D. W. Cameron and E. L. Samuel, Austral. J. Chem.,29, 2499 (1976).
A. F. Pozharskii and I. S. Kashparov, Khim. Geterotsikl. Soedin., No. 1, 111 (1970).
A. K. Sheinkman, A. F. Pozharskii, V. I. Sokolov, and T. V. Stupnikova, Dokl. Akad. Nauk SSSR,226, 1094 (1976).
I. V. Komissarov, A. A. Konstantinchenko, A. F. Pozharskii, I. T. Filippov, and I. S. Kashparov, Khim.-Farm. Zh.,28, No. 7, 28 (1976).
A. F. Pozharskii, G. G. Yurchuk, and L. L. Gervits, Khim. Geterotsikl. Soedin., No. 3, 413 (1979).
A. F. Pozharskii and I. S. Kashparov, Khim. Geterotsikl. Soedin., No. 6, 859 (1972).
V. I. Sokolov, A. F. Pozharskii, I. S. Kashparov, A. G. Ivanov, and B. I. Ardashev, Khim. Geterotsikl. Soedin., No. 4, 558 (1974).
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See [1] for communication 48.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 684–690, May, 1980.
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Klyuev, N.A., Pozharskii, A.F., Belikov, A.B. et al. Heterocyclic analogs of pleiadiene. 49. Mass spectra of some N-substituted perimidines and 2,3-dihydroperimidines. Chem Heterocycl Compd 16, 535–540 (1980). https://doi.org/10.1007/BF00561356
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DOI: https://doi.org/10.1007/BF00561356