775303-52-1Relevant academic research and scientific papers
First stable O-amidinylhydroxylamines and their transformations into sulfenamides by intramolecular 1,5-O→S amine migration
Saczewski, Franciszek,Kornicka, Anita,Gdaniec, Maria,Halasa, Rafal,Werel, Wladyslaw
, p. 3511 - 3516 (2007/10/03)
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→S amine migration involves the tandem nucleophilic addition-electrophilic amination reaction. The intermolecular version of this process using preformed triethylammonium dithiocarbamates gives the corresponding sulfenamides 14-16. Functionalized ethylenediamines 17-19 are obtained by treatment of 8 and 9 with amines. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
