Abstract
1-Methylperimidine adds phenylsodium and phenyllithium to the C=N bond to give 1-methyl-2-phenyl-2, 3-dihydroperimidines. However, if benzophenone is present in the reaction mixture, a mixture of 1-methyl-2-phenylperimidine and l-methyl-2, 4-diphenylperimidine (when phenylsodium is used) or l-methyl-2-phenyl-4-(α-hydroxybenzhydryl)perimidine (when phenyllithium is used) is formed. It is assumed that the formation of products involving substitution in the naphthalene ring is associated with the participation of C6H5 and (C6H5)2C-O− radical particles that are formed on reaction of the phenylmetallic compound with benzophenone.
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T. I. Vinokurova and A. F. Pozharskii, Khim. Geterotsikl. Soedin., No. 4, 545 (1976).
A. F. Pozharskii, L. P. Smirnova, B. A. Tertov, I. S. Kashparov, and V. I. Sokolov, Khim. Geterotsikl. Soedin, No. 12, 1682 (1975).
A. F. Pozharskii, I. S. Kashparov, P. J. Halls, and V. G. Zaletov, Khim. Geterotsikl. Soedin., No. 4, 543 (1971).
A. F. Pozharskii, I. V. Borovlev, and I. S. Kashparov, Khim. Geterotsikl. Soedin., No. 4, 543 (1975).
W. Schlenk and R. Ochs, Ber., 49, 608 (1916).
W. Schlenk and E. Bergmann, Ann., 1, 464 (1928).
A. E. Arbuzov and I. A. Arbuzova, Zh. Obshch. Khim., No. 3, 388 (1932).
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See [1] for communication XXIII.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 697–701, May, 1976.
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Smirnova, L.P., Pozharskii, A.F. & Borovlev, I.V. Heterocyclic analogs of pleiadiene. Chem Heterocycl Compd 12, 586–590 (1976). https://doi.org/10.1007/BF00470119
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DOI: https://doi.org/10.1007/BF00470119