Abstract
Pyrolysis (320–370 °C) of polycyclic 1-pyrazolines1 and2, obtained by 1,3-dipolar cycloaddition of diazocyclopropane to 3,3-dimethylcyclopropene and spiro[2,3]hex-1-ene, yields complex mixtures of isomeric hydrocarbons, substituted methylenecyclopropanes being the main components. Pyrolysis of 6-ethenyl- (4) and 6-methoxy-6-methylcarbonyl-4,5-diazaspiro[2,4]hept-4-enes (6) at 310–320 °C proceeds more unambiguously to give vinyl- (18) and 1-methoxy-1-methylcarbonylspiropentanes (20) in ∼85 and 95 % yields with respect to the transformed pyrazolines. Dediazotization of pyrazoline3 obtained from diazocyclopropane and benzvalene requires more drastic conditions (−440 °C) and produces indane.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2203–2207, 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., Yarygin, S.A. et al. Thermal decomposition of strained spiro(1-pyrazoline-3,1′-cyclopropanes). Russ Chem Bull 44, 2109–2113 (1995). https://doi.org/10.1007/BF00696714
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DOI: https://doi.org/10.1007/BF00696714