Thermolysis of 1-phthalimidoaziridine-2-carbonitriles in the presence of dipolarophiles |
| |
Authors: | M A Kuznetsov A S Pan’kova A V Ushkov S I Selivanov |
| |
Institution: | (1) St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia |
| |
Abstract: | Thermolysis of trans-3-phenyl-1-phthalimidoaziridine-2-carbonitrile and trans-1-phthalimidoaziridine-2,3-dicarbonitrile in the presence of several dipolarophiles involves 1,3-dipolar cycloaddition to intermediate azomethine ylides and leads to 1-phthalimidopyrrolidine derivatives with good yields and high stereoselectivity. Thermally induced opening of the three-membered ring in trans-2,3-disubstituted 1-phthalimidoaziridines occurs in conrotatory mode to produce the corresponding cis-azomethine ylides in keeping with the orbital symmetry conservation rules. The relative configuration of substituents in the dipolarophiles is retained, which implies concerted mechanism of the addition. |
| |
Keywords: | |
本文献已被 SpringerLink 等数据库收录! |
|