14843-83-5Relevant academic research and scientific papers
Reactions of Halogenated Methanesulfonyl Chlorides with Trimethylamine and an Inverse Sulfene-Amine Adduct
Rheude, Udo,Sundermeyer, Wolfgang
, p. 2208 - 2219 (2007/10/02)
Starting from chlorofluoromethane (3), prepared by a convenient procedure, fluoromethanesulfonyl chloride (6) was synthesized easily and cleanly via the intermediate thioethers 4-chlorobenzyl fluoromethyl sulfide (4) or benzhydryl fluoromethyl sulfide (5) for the first time.Reaction of 6 with trimethylamine leads to an inverse amine-adduct 9a of fluorosulfene, which was characterized by transformation to (fluoromethyl)trimethylammonium chloride (10) and by oxidation to the sulfonate 11.The structure of 9a is discussed on the basis of spectroscopic data.Bromomethanesulfonyl chloride (17) similarly as chloromethanesulfonyl chloride leads to a dimeric adduct 18a of (bromomethylsulfonyl)sulfene and trimethylamine, which is characterized by its hydrolysis product 19a. 2,4-Dibromo-1,3-dithietane 1,1,3,3-tetraoxide (15) could not be detected, but has been prepared by another method.The products, resulting from the monohalogenmethanesulfonyl chlorides, can be explained by the intermediate existence of the monohalogensulfenes.Difluoro- (20) and dichloromethanesulfonyl chloride (24) gave no sulfeneamine adducts; 20 yields (difluoromethyl)trimethylammonium chloride and other products while from 24 under various conditions only trimethylammonium trichloromethanesulfinate (25) is formed.
