The Journal of organic chemistry

Synthesis and aqueous chemistry of α-acetoxy-N-nitrosomorpholine: Reactive intermediates and products

CN Zink, HJ Kim, JC Fishbein

Index: Zink, Charles N.; Kim, Hyun-Joong; Fishbein, James C. Journal of Organic Chemistry, 2006 , vol. 71, # 1 p. 202 - 209

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Citation Number: 5

Abstract

α-Acetoxy-N-nitrosomorpholine (7) has been synthesized starting by the anodic oxidation of N-acetylmorpholine in methanol. The 55% yield of N-nitrosomorpholinic acid, after cyanide- for-methoxy group exchange and hydrolysis, is an improvement of~ 10-fold over our original 10-step method, and this is readily converted to 7. A study of the kinetics of decomposition of 7 in aqueous media at 25° C and 1 M ionic strength was conducted over the pH range ...