Reaction of diazoalkanes with unsaturated compounds. 10. 1,3-Dipolar cycloaddition of diazocyclopropane to strained cycloalkenes

Reaction of diazoalkanes with unsaturated compounds. 10. 1,3-Dipolar cycloaddition of diazocyclopropane to strained cycloalkenes Full article

Journal

Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science
ISSN: 2376-8444 , E-ISSN: 0568-5230

Output data

Year: 1991, Volume: 40, Number: 5, Pages: 939-944 Pages count : 6 DOI: 10.1007/bf00961354

Authors

Tomilov Yu.V. ¹ , Shulishov E.V. ¹ , Nefedov O.M. ¹

Affiliations

1	N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

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.

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
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1991. V.40. N5. P.939-944. DOI: 10.1007/bf00961354 OpenAlex

≡ OpenAlex:

W2950110125