Journal of the American Chemical Society

The Alleged Role of Nitroxyl in Certain Reactions of Aldehydes and Alkyl Halides1

PAS Smith, GE Hein

Index: Smith,P.A.S.; Hein,G.E. Journal of the American Chemical Society, 1960 , vol. 82, p. 5731 - 5740

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Citation Number: 117

Abstract

The reaction of primary alkyl halides with Piloty's acid (C&SO* h'HOH) or Angeli's salt (NarN20t). reported by Angeli to give aldoximes. has been shown to proceed by alkylation of the beuzenesulfonhydroxamate or nitrohydroxamate ion, respectively, rather than by alkylation of nitroxyl, HNO. which these compounds generate. Sodium nitrosyl does not convert alkyl halides to oximes, nor does it convert aldehydes to hydroxamic acids (Aageli ...