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The Preparation of Stable α‐Chlorosulfenyl Chlorides from Sterically Crowded Tetramethylcyclobutanethiones and Chlorine
Author(s) -
Norup Koch Kristian,
Mloston Grzegorz,
Senning Alexander
Publication year - 1999
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/(sici)1099-0690(199901)1999:1<83::aid-ejoc83>3.0.co;2-9
Subject(s) - chemistry , steric effects , chlorine , adduct , chlorine atom , organic chemistry , medicinal chemistry , polymer chemistry
The sterically crowded 2,2,4,4‐tetramethyl‐3‐thioxocyclobutanone ( 7 ) and its dithio analogue 9 were found to react readily with gaseous chlorine to afford 1:1 and 1:2 adducts, respectively. The stable, crystalline products were identified as the α‐chlorosulfenyl chlorides 8 and 12 which yielded corresponding disulfides after treatment with equimolar amounts of thioacetic acid.