1-Alkenesulfinyl Chlorides:  Synthesis, Characterization, and Some Substitution Reactions

Abstract

A number of 1-alkenyl sulfoxides bearing either a diphenylmethyl (DPM) or a p -methoxybenzyl (PMB) group have been prepared and exposed to the chlorine surrogate SO 2 Cl 2 . Through an oxidative fragmentation reaction, a new family of sulfur acid derivatives, 1-alkenesulfinyl chlorides, is generated. They can be characterized by IR spectroscopy before chemical capture with an alcohol. Ethenesulfinyl chloride ( 2a ) and 1-propenesulfinyl chloride ( 2b ), obtained from their corresponding DPM precursor, can be distilled at reduced pressure to afford ca. 90% pure material. NMR chemical shift comparison of various 1-alkenesulfinyl-containing compounds is made. 1-Alkenesulfinylmethyl phenyl(alkyl) ketones ( 6 ) can be prepared directly from sulfinyl chlorides 2 although decomposition and/or isomerization is sometimes extensive during purification.