Journal of Organic Chemistry p. 1302 - 1305 (1986)
Update date:2022-08-11
Topics:
Griesbaum, Karl
Scaria, Pallikaparampil M.
Doehling, Thomas
Reaction of trans-2,3-dichlorooxirane (1) with dimethyl sulfide afforded in high yield dimethyl(1-chloro-2-hydroxyethenyl)sulfonium chloride (2a).The latter was converted into 1-chloro-2-methoxy-1-(methylthio)ethene (3b) and into 2-acetoxy-1-chloro-1-(methylthio)ethene (3c) by reaction with diazomethane and with ketene, respectively.Pyrolysis of 2a gave chloro(methylthio)acetaldehyde (4a) and dichloroacetaldehyde (6), along with a series of minor byproducts.
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