Single electron transfer versus nucleophilic ring opening in reactions of cis-trans pairs of activated 2-phenylaziridines. Strong influence of nitrogen pyramid for N- …

R Falkenstein, T Mall, D Speth…

Index: Falkenstein, Reinhard; Mall, Thomas; Speth, Dieter; Stamm, Helmut Journal of Organic Chemistry, 1993 , vol. 58, # 26 p. 7377 - 7381

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Citation Number: 12

Abstract

X'E xanthyl radical amidoethylated xanthene in one case (R= Me) is evidence for a cross combination of X'with the radical formed by homolytic ring opening. Cross combination is also a likely path for R= H (no cis-trans isomerism), in addition to reductive ring opening. cis- Aziridines with dimethylcarbamoyl on nitrogen do not react via SET since the ketyl is not stabilized and therefore difficult to generate. Carbonyl attack on both types of ...