PERHALOALKANESULFINYL CHLORIDES, RFS(O)CL, AND PERHALOALKANESULFINATE ESTERS, RFS(O)ORF'

Five halogenated methane- and ethanesulfinyl chlorides, R(f)S(O)Cl (R(f) = CCl3, CFCl2, CF2Cl, CF3CCl2, CF3CBrCl) have been prepared by reacting the respective sulfinic acids, R(f)S(O)OH, with SOCl2. The sulfinyl chlorides have been converted to a series of new stable halogenated sulfinyl esters R(f)S(O)OR(f)' R(f)' = CF3CH2, CH3(CF3)CH, C(CF3)2CH3, C6H5) by treatment with fluoro alcohols or phenol in the presence of pyridine or triethylamine. The tert-butyl sulfinates (R(f) = CFCl2, CF3CCl2; R(f)' = C(CH3)3) decompose upon distillation to give isobutylene and the parent sulfinic acid. Complex nuclear magnetic resonance spectra are observed for the esters with chiral centers at sulfur and carbon.