Journal of the American Chemical Society p. 744 - 747 (1980)
Update date:2022-08-02
Topics:
Cameron, Tim B.
Pinnick, Harold W.
Flash vacuum pyrolysis of 1,3-oxathiolan-5-ones causes loss of carbon dioxide with the concominant formation of the corresponding thiiranes in nearly quantitative yield.The reaction is stereospecific and proceeds by clean inversion of configuration.This suggests a concerted loss of carbon dioxide.Furthermore, substituent effects strongly support the intermediacy of thiocarbonyl ylides.Consequently, this method becomes one of the simplest ways of generating these species.
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