1-Alkenesulfinyl Chlorides: Synthesis, Characterization, and Some Substitution Reactions
摘要:
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
摘要:
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. Copyright (C) 1996 Elsevier Science Ltd
1-Alkenesulfinyl Chlorides: Synthesis, Characterization, and Some Substitution Reactions
作者:Adrian L. Schwan、Rick R. Strickler、Yvonne Lear、Mark L. Kalin、Tanya E. Rietveld、Ting-Jian Xiang、Denis Brillon
DOI:10.1021/jo980970t
日期:1998.10.1
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
作者:Adrian L. Schwan、Mark L. Kalin、Kristin E. Vajda、Ting-Jian Xiang、Denis Brillon
DOI:10.1016/0040-4039(96)00281-x
日期:1996.4
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. Copyright (C) 1996 Elsevier Science Ltd