Abstract
Polycyclic spiro(1-pyrazoline-3,1′-cyclopropanes) were obtained in 32–70 % yields by the reaction of diazocyclopropane generatedin situ with 2-methyltricyclo[3.2.1.02,4]oct-6-ene, spiro[2,4]hepta-4,6-diene dimer, benzvalene, spiro[2,3]hex-1-ene, methyl 1-methylcyclopropene-3-carboxylate, buta-1,3-diene, and 2-methylbuta-1,3-diene.
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References
P. Bladon and D. R. Rae,J. Chem. Soc., Perkin Trans, 1, 1974, 2240.
P. Bladon and D. R. Rae,J. Chem. Soc., Perkin Trans. 1, 1975, 2460.
Yu. V. Tomilov, E. V. Shulishov, and O. M. Nefedov,Izv. Akad. Nauk SSSR, Ser. Khim., 1991, 1057 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991,40, 939 (Engl. Transl.)].
C. J. Rostek and W. M. Jones,Tetrahedron Lett., 1969, 3957.
L. Fitjer and J. M. Conia,Angew. Chem.,1973, 85, 349.
P. Bladon, D. R. Rae, and A. D. Tait,J. Chem. Soc., Perkin Trans. 1, 1974, 1468.
L. Fitjer and D. Wehle,Chem. Ber., 1982,115, 1061.
S. Zöllner, H. Buchholz, R. Boese, R. Gleiter, and A. de Meijere,Angew. Chem., 1991,103, 1544.
Iteratsionnaya programma CALM. Produktsiya MP “Rezonans” (Iteration Program CALM. Small Venture “Rezonans” Product), Moscow.
R. J. Crawford and D. M. Cameron,Can. J. Chem., 1967,45, 691.
R. I. Khusnutdinov, V. A. Dokichev, D. K. Galeev, N. F. Asylguzhina, S. Z. Sultanov, and U. M. Dzhemilev,Izv. Akad. Nauk SSSR, Ser. Khim., 1988, 2152 [Bull. Acad. Sci. USSR., Div. Chem. Sci., 1988,37, 1932 (Engl. Transl.)].
N. I. Yakushkina and I. G. Bolesov,Zh. Org. Khim., 1979.15, 954.
I. E. Dolgii, G. P. Okonnishnikova, E. A. Baidzhigitova, and O. M. Nefedov,Izv. Akad. Nauk SSSR, Ser. Khim., 1977, 2592 [Bull. Acad. Sci. USSR., Div. Chem. Sci., 1977,26, 2401 (Engl. Transl.)].
W. Kirmse and H. Schütte,Chem. Ber., 1968,101, 1674.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2199–2202, November, 1995.
This study was financially supported by the Russian Foundation for Basic Research (Grant No. 94-03-08902).
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Tomilov, Y.V., Shulishov, E.V., Okonnishnikova, G.P. et al. 1,3-Dipolar cycloaddition of diazocyclopropane to strained cycloalkenes and conjugated dienes to give spiro(1-pyrazoline-3,1′-cyclopropanes). Russ Chem Bull 44, 2105–2108 (1995). https://doi.org/10.1007/BF00696713
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DOI: https://doi.org/10.1007/BF00696713