Competitive base-induced. alpha.-elimination and methanolysis of N-aryl-O-pivaloylhydroxylamines

M Novak, KA Martin, JL Heinrich, KM Peet…

Index: Novak, Michael; Martin, Kristy A.; Heinrich, Julie L.; Peet, Kristine M.; Mohler, Linda K. Journal of Organic Chemistry, 1990 , vol. 55, p. 3023 - 3028

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Citation Number: 8

Abstract

The N-aryl-0-pivaloylhydroxylamines la-c are quite stable in MeOH under neutral conditions, but under mildly basic conditions (0.05 M EtzNH or Et3N) they undergo rapid decomposition (tllz= 3-5 h at 25'C) by two competitive processes: apparent a-elimination to generate the nitrenes 2a-c and pivalic acid and basic ester methanolysis to generate the hydroxylamines 3a-c and methyl pivalate. The nitrenes decompose into the corresponding anilines 5 and ...