Cascade dimerization of 2-styryl-1,1-cyclopropanedicarboxylate upon treatment with gallium trichloride

Cascade dimerization of 2-styryl-1,1-cyclopropanedicarboxylate upon treatment with gallium trichloride Full article

Journal

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

Output data

Year: 2016, Volume: 65, Number: 11, Pages: 2628-2638 Pages count : 11 DOI: 10.1007/s11172-016-1628-0

Authors

Novikov R.A. ¹ , Tarasova A.V. ¹ , Denisov D.A. ¹ , Korolev V.A. 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

2-Styrylcyclopropane-1,1-dicarboxylate treated with anhydrous gallium trichloride undergoes dimerization with the cyclopropane ring opening and the styryl substituent double bond involvement, leading to the formation of polysubstituted cyclic and bicyclic structures with the predominance of the former or the latter depending on the reaction conditions. Most compounds are formed with very high diastereoselectivity. Thirteen major and minor dimeric structures were isolated and reliably characterized, two of which were found to additionally include a chlorine atom. A rare for the reactions of donor-acceptor cyclopropanes example of the formation of a product with the fused cyclobutane ring was effected at–80 °C. Plausible mechanisms of observed processes were discussed.

Novikov R.A. , Tarasova A.V. , Denisov D.A. , Korolev V.A. , Tomilov Y.V.
Cascade dimerization of 2-styryl-1,1-cyclopropanedicarboxylate upon treatment with gallium trichloride
Russian Chemical Bulletin. 2016. V.65. N11. P.2628-2638. DOI: 10.1007/s11172-016-1628-0 WOS Scopus OpenAlex

≡ Web of science:	WOS:000401572700011
≡ Scopus:	2-s2.0-85019216283
≡ OpenAlex:	W2615050516