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On Alkylideneamidosulfenyl Chlorides and 1‐Thia‐2‐azoniaallene Salts
Author(s) -
Wirschun Wolfgang G.,
Hitzler Martin G.,
Jochims Johannes C.,
Groth Ulrich
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200209)85:9<2627::aid-hlca2627>3.0.co;2-h
Subject(s) - chemistry , sulfenamide , morpholine , medicinal chemistry , chloride , stereochemistry , salt (chemistry) , crystallography , organic chemistry , natural rubber , vulcanization
X‐Ray‐diffraction analysis of t Bu 2 CNSCl ( 4b ) revealed an almost linear CNS unit with an SN bond order of ca. 1.9 ( Fig. 1 ), in agreement with the structure of a 1‐thia‐2‐azoniaallene chloride. With SCl 2 and SbCl 5 , compound 4b was transformed into the imidosulfurous dichloride 6 ( Scheme 2 ). With morpholine, compounds 4b and 6 afforded the sulfenamide 7 and the aminosulfonium salt 8 , respectively. The (diarylmethylene)amidosulfenyl chlorides 4g , h , i reacted with SbCl 5 to give SbCl salts of the 1,2‐benzisothiazoles 9a , b , d , most likely via 1‐thia‐2‐azoniaallene intermediates 2 ( Scheme 3 ).