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Die Fluorsulfine XF 2 C(F)C SO (X = F, Cl, Br), ihre Synthese und ungewöhnliche Zersetzungsart
Author(s) -
Gradel Jan,
Sundermeyer Wolfgang
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250816
Subject(s) - chemistry , thermal decomposition , adduct , anthracene , medicinal chemistry , decomposition , hydrolysis , trifluoromethyl , stereochemistry , photochemistry , organic chemistry , alkyl
The Fluorosulfines XF 2 C(F)C SO (X = F, Cl, Br), Their Synthesis and Unusual Type of Decomposition A new route for the synthesis of the sulfenyl chloride 3 opens an easy access to fluoro(trifluoromethyl)sulfine ( 6 ) by hydrolysis of 3 , trapping 6 by Diels‐Alder reaction with anthracene, and thermolysis of the formed compound 8 . By addition of the thioacetyl fluorides XF 2 C(F)C S (X = Cl, Br) to anthracene compounds 9a, b are obtained, which could be oxidized to the sulfene adducts 12a, b as well as to the sulfine adducts 13a, b . Thermolysis of the latter yields the sulfines 17a, b , which are unstable at room temperature. A second approach to 17a involves oxidation of 1,3‐dithietane 11a to its S ‐oxide 14a (e.g. via an S,S ‐difluoro compound 15a ) and subsequent thermolysis, but thermal decomposition predominates. An unusual decomposition has been observed for 17a, b which was hitherto unknown for sulfines.