176907-95-2Relevant academic research and scientific papers
1-alkenesulfinyl chlorides: Synthesis, characterization, and some substitution reactions
Schwan, Adrian L.,Strickler, Rick R.,Lear, Yvonne,Kalin, Mark L.,Rietveld, Tanya E.,Xiang, Ting-Jian,Brillon, Denis
, p. 7825 - 7832 (2007/10/03)
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 SO2Cl2. 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.
Oxidative fragmentations of selected 1-alkenyl sulfoxides. Chemical and spectroscopic evidence for 1-alkenesulfinyl chlorides
Schwan, Adrian L.,Kalin, Mark L.,Vajda, Kristin E.,Xiang, Ting-Jian,Brillon, Denis
, p. 2345 - 2348 (2007/10/03)
A collection of 1-alkenyl sulfoxides possessing diphenylmethyl, p-methoxybenzyl or 2-(trimethylsilyl)ethyl groups can be converted to 1-alkenesulfinyl chlorides using SO2Cl2. The 1-alkenesulfinyl chlorides were spectroscopically characterized by IR and were chemically captured as their cyclohexyl or 3-phenylpropyl 1-alkenesulfinate esters.
