Heavy-atom kinetic isotope effects in the acid-catalyzed rearrangement of N-2-naphthyl-N'-phenylhydrazine. Rearrangement is shown to be a concerted process

HJ Shine, L Kupczyk-Subotkowska…

Index: Shine, Henry J.; Kupczyk-Subotkowska, Lidia; Subotkowski, Witold Journal of the American Chemical Society, 1985 , vol. 107, # 23 p. 6674 - 6678

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Citation Number: 31

Abstract

Abstract: Heavy-atom kinetic isotope effects (KIE) have been measured in the acid-catalyzed rearrangement of N-2-naphthyl-”-phenylhydrazine (1) into l-(o-aminophenyl)-2- naphthylamine (2). A combination of whole-molecule-ion and isotope ratio mass spectrometry and scintillation counting has given KIE for I5N,” C, and I4C. Use of [15N,” N'] 1 and whole-molecule-ion mass spectrometry gave a KIE of 1.0434 (for two I5N atoms). Use ...