SN2 substitution reactions at the amide nitrogen in the anomeric mutagens, N-acyloxy-N-alkoxyamides

…, SA Glover, HL Price, RR Schumacher

Index: Cavanagh, Katie L.; Glover, Stephen A.; Price, Helen L.; Schumacher, Rhiannon R. Australian Journal of Chemistry, 2009 , vol. 62, # 7 p. 700 - 710

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Citation Number: 17

Abstract

Abstract N-Acyloxy-N-alkoxyamides 1a are unusual anomeric amides that are pyramidal at the nitrogen because of bis oxyl substitution. Through this configuration, they lose most of their amide character and resemble α-haloketones in reactivity. They are susceptible to SN 2 reactions at nitrogen, a process that is responsible for their mutagenic behaviour. Kinetic studies have been carried out with the nucleophile N-methylaniline that show that, like SN ...