Journal of the American Chemical Society

Amine Oxides. I. Gramine Oxide1

DW Henry, E Leete

Index: Henry; Leete Journal of the American Chemical Society, 1957 , vol. 79, p. 5254

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Citation Number: 27

Abstract

Treatment of gramine with hydrogen peroxide yields gramine oxide (I). On heating, gramine oxide rearranges to 0-skatyl-N, N-dimethylhydroxylamine (11). Nucleophilic reagents (amines, alkoxides, hydroxide, cyanide and the nitromethyl anion) react with gramine oxide yielding the corresponding skatyl derivatives and N, N-dimethylhydroxylamine. Gramine oxide decomposes in water at 100” yielding 3, 3'-diindolylmethane, formaldehyde and ...

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