Treatment of diazoalkanes with unsaturated compounds. No. 5. Catalytic cyclopropanation of unsaturated hydrocarbons with diazoethane

Treatment of diazoalkanes with unsaturated compounds. No. 5. Catalytic cyclopropanation of unsaturated hydrocarbons with diazoethane 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: 1987, Volume: 36, Number: 6, Pages: 1234-1239 Pages count : 6 DOI: 10.1007/bf00956669

Authors

Tomilov Yu.V. ¹ , Bordakov V.G. ¹ , Lutsenko A.I. ¹ , Kozhinskii S.O. ¹ , Dolgii I.E. ¹ , Nefedov O.M. ¹

Affiliations

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

The preparative catalytic cyclopropanation of unsaturated hydrocarbons with diazoethane has been achieved for the first time. Addition of the ethylidene fragment to the C=C double bond occurs in a nonstereoselective manner and leads to the formation of the corresponding methylcyclopropanes in 55–70% total yields. In the presence of CuCl, all double bonds of unsaturated hydrocarbons are cyclopropanated with equal facility, whereas in the presence of (PhCN)2PdCl2, preferential regioselective cyclopropanation of strained endocyclic and terminal double bonds is observed, just as was true in the case of reactions with diazomethane.

Tomilov Y.V. , Bordakov V.G. , Lutsenko A.I. , Kozhinskii S.O. , Dolgii I.E. , Nefedov O.M.
Treatment of diazoalkanes with unsaturated compounds. No. 5. Catalytic cyclopropanation of unsaturated hydrocarbons with diazoethane
Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science. 1987. V.36. N6. P.1234-1239. DOI: 10.1007/bf00956669 OpenAlex

≡ OpenAlex:

W1988695898