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

Sączewski Franciszek | Zendy; Kornicka Anita | Zendy; Gdaniec Maria | Zendy; Hałasa Rafal | Zendy; Werel Władyslaw | Zendy

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

Author(s) -

Sączewski Franciszek,

Kornicka Anita,

Gdaniec Maria,

Hałasa Rafal,

Werel Władyslaw

Publication year - 2004

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200400229

Subject(s) - chemistry , intramolecular force , amine gas treating , amination , carbon disulfide , nucleophile , intermolecular force , medicinal chemistry , electrophile , disulfide bond , polymer chemistry , organic chemistry , molecule , catalysis , biochemistry

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)

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