sulfene
Sign in to saveSulfene is an extremely reactive chemical compound with the formula H2C=SO2. It is the simplest member of the sulfenes, the group of compounds which are S,S-dioxides of thioaldehydes and thioketones, and have the general formula R2C=SO2.
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4 sectionsContents
- Preparation
- Reactions
- See also
- References
Sulfene is an extremely reactive chemical compound with the formula H2C=SO2. It is the simplest member of the sulfenes, the group of compounds which are S,S-dioxides of thioaldehydes and thioketones, and have the general formula R2C=SO2.
==Preparation== The first general method for preparation of sulfene as an intermediate, reported simultaneously in 1962 by Gilbert Stork and by Günther Optiz, involved the removal of hydrogen chloride from methanesulfonyl chloride using triethylamine in the presence of an enamine as trapping agent. The formation of a thietane 1,1-dioxide derivative was taken as evidence for the intermediacy of sulfene. Because of the highly electrophilic character of sulfene, the use of amines presents difficulties, since they can intercept the sulfene to form adducts. A simple alternative which avoids the use of amines involves desilylation of trimethylsilylmethanesulfonyl chloride with cesium fluoride in the presence of trapping agents. (CH3)3SiCH2SO2Cl + CsF → [CH2=SO2] + (CH3)3SiF + CsCl