Synthesis and photolysis of N-phthalimidoaziridines with electron-withdrawing substituents

Fused aziridines as sources of azomethine ylides

“…In a series of papers the photolysis of aziridines 81, fused with the succinimide system, in the presence of DMAD was investigated, and, as a result, products from cycloaddition of the ylides 82 to the triple bond, i.e., 3,8-diazabicyclo[3.2.1]octanes 83, were obtained. The yields of compounds 83 depend strongly on the substituent at the nitrogen atom both in the aziridine part and in the pyrrolidinedione part of the molecule: R = Me, R 1 = 4-МеОС 6 Н 4 -70% [33], R = Bn, R 1 = 4-MeOC 6 H 4 -~6% [34], R = Bn, R 1 = phthalimido -13% [35]. The ylide 82 (R = Me, R 1 = 4-MeOC 6 H 4 ) gives a mixture of the isomeric exo adducts and norbornene with a yield of 33% [33].…”