Catalytic reaction of dicyclopropylacetylene with diazomethane: synthesis of ivyane[4]

Catalytic reaction of dicyclopropylacetylene with diazomethane: synthesis of ivyane[4] Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2025, Volume: 74, Number: 3, Pages: 865-870 Pages count : 6 DOI: 10.1007/s11172-025-4580-z

Authors

Shulishov E.V. ¹ , Pantyukh O.A. ¹ , Streltsova E.D. ¹ , Menchikov L.G. ¹ , Tomilov Yu.V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

The reaction of dicyclopropylacetylene with excess diazomethane in the presence of copper compounds leads successively first to dicyclopropylcyclopropene resulting from multiple bond cyclopropanation and then to 1,3-dicyclopropylbicyclo[1.1.0]butane. The latter under the reaction conditions partially isomerizes to 2,3-dicyclopropylbuta-1,3-diene, which, in turn, undergoes further cyclopropanation. As a result, when an 8–10-fold excess of diazomethane is used, a hydrocarbon of the 1,1-oligocyclopropane series, 1,1′-dicyclopropylbicyclopropane (ivyane[4]), is formed. Monocyclopropanation of dicyclopropylbutadiene readily proceeds in the presence of Pd(acac)2, whereas cyclopropanation of the second double bond occurs only with a large excess of diazomethane.

Shulishov E.V. , Pantyukh O.A. , Streltsova E.D. , Menchikov L.G. , Tomilov Y.V.
Catalytic reaction of dicyclopropylacetylene with diazomethane: synthesis of ivyane[4]
Russian Chemical Bulletin. 2025. V.74. N3. P.865-870. DOI: 10.1007/s11172-025-4580-z WOS Scopus OpenAlex

≡ Web of science:	WOS:001478277500009
≡ Scopus:	2-s2.0-105003768473
≡ OpenAlex:	W4409886511