Abstract
Abstract Dihalogenomethylene sulfoxides (dihalogenosulfines) 2a – c were generated by flash vacuum pyrolysis of 2,2,4,4-tetrahalogeno-1,3-dithietane 1,3-dioxides 1a – c and trapping the pyrolysis products in argon at 10 K. At room temperature unstable difluorosulfine ( 2a ) and chlorofluorosulfine ( 2b ) were identified by i.r. spectroscopy, and the photochemistry of the sulfines was investigated. Chlorofluorosulfine ( 2b ) exists in two geometrical isomers. Photolysis of 2a leads to fragmentation to give CF 2 and SO, photolysis of the chlorine containing sulfines 2b and 2c to rearrangement to give the sulfenyl chlorides 6 and 8 . This is explained by different migratory tendencies of fluorine and chlorine and the stability of the CF bond.
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