Characterisierung und Photochemie von (Dihalogenmethylen)sulfoxiden, XYC=S=O

Article abstract of DOI:10.1016/0584-8539(86)80227-6

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 CF2 and SO, photolysis of the chlorine containing sulfines 2b and 2c to rearrangement to give sulfenyl chlorides 6 and 8.This is explained by different migratory tendencies of fluorine and chlorine and the stability of C-F bond.