Abstract
The reaction of diazocyclopropane, generated in situ by alkaline hydrolysis of N-nitroso-N-cyclopropylurea at −20‡ to −40‡C, with the double bond of norbornene hydrocarbons or 3,3-dimethylcyclopropene is a 1,3-dipolar cycloaddition and affords 45–70% yields of thermally stable 1-pyrazolines possessing a spiro-joined cyclopropane fragment. Methylenecyclopropane under the same conditions is a less effective and selective interceptor of diazocyclopropane, forming in ∿ 10% yields not only isomeric 1-pyrazolines but the corresponding product of cyclopropylization, dispiro[2.0.2.1]heptane.
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For previous communication, see [1].
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1057–1062, May, 1991.
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Tomilov, Y.V., Shulishov, E.V. & Nefedov, O.M. Reaction of diazoalkanes with unsaturated compounds. 10. 1,3-Dipolar cycloaddition of diazocyclopropane to strained cycloalkenes. Russ Chem Bull 40, 939–944 (1991). https://doi.org/10.1007/BF00961354
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DOI: https://doi.org/10.1007/BF00961354