First Stable O??Amidinylhydroxylamines and Their Transformations into Sulfenamides by Intramolecular 1, 5??O→ S Amine Migration

…, A Kornicka, M Gdaniec, R Hałasa…

Index: Saczewski, Franciszek; Kornicka, Anita; Gdaniec, Maria; Halasa, Rafal; Werel, Wladyslaw European Journal of Organic Chemistry, 2004 , # 16 p. 3511 - 3516

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Citation Number: 2

Abstract

Abstract The reaction of 2-chloro-4, 5-dihydroimidazole (1) with aliphatic hydroxylamines 2− 4 gives O-amidinylhydroxylamines 5− 7 in contrast to the analogous reaction of 1 with N- arylhydroxylamines in which N-substitution occurs. A number of thiocarbamoylsulfenamides 8− 10 have been prepared by the reaction of 5− 7 with carbon disulfide under basic and mild conditions. The key step in the 1, 5-O [RIGHTWARDS ARROW] S amine migration ...