page_title: Sulfene
section_title: Preparation
hierarchical_section_title: Sulfene / Preparation
caption_attribution_description: English: Structure of (H2N)2C=SO2 from doi 10.1107/S0365110X62001851.
context_page_description: 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.
context_section_description: The first general method for preparation of sulfene as an intermediate, reported simultaneously in 1962 by Gilbert Stork and by Günther Optiz, involved 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
  Alternatively, sulfenes can be stabilized by installing amido substituents on the alkylidene substituent.  The extreme case is thiourea dioxide, which features planar amido groups.
caption: Structure of thioureadioxide ((H2N)2CSO2). Selected distances and angles: rS=O = 1.49, rS=C = 1.85.1, rC-N = 1.31 Å, sum of angles around S = 112°.[7]
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