Reactions with aziridines. 33. Arene hydrides. Part 1. Highly regioselective ring cleavage of N-acylaziridines by" anthracene hydride"(anion of 9, 10- …

…, A Sommer, A Woderer, W Wiesert, T Mall…

Index: Stamm, Helmut; Sommer, Andreas; Woderer, Anton; Wiesert, Wolfgang; Mall, Thomas; Assithianakis, Petros Journal of Organic Chemistry, 1985 , vol. 50, # 24 p. 4946 - 4955

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Citation Number: 34

Abstract

Anthracene hydride AH-reacts with N-acylaziridines by reductive opening of the aziridine ring and/or amidoethylation of AH-. When the two aziridine carbons are differently substituted, in both reactions only that bond is broken which can form the more stable carbon radical quite in accord with the intermediacy of a radical anion (ketyl) 14 and with the known homolytic cleavage of 14 forming the radical 15. The extra electron in 14 is ...