Sulfonyl halide

Sulfonyl halide groups occur when a sulfonyl functional group is singly bonded to a halogen atom. They have the general formula R-SO2-X where X is a halogen.

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Sulfonyl fluorides

Sulfonyl fluorides have the general formula R-SO2-F and can be important sulfonyl halide synthetic precursors. For example, "most, if not all" industrially synthesized perfluorooctanesulfonyl derivatives, such as PFOS, have the sulfonyl fluoride as their precursor.[1]

Sulfonyl chlorides

Sulfonic acid chlorides, or sulfonyl chlorides, are a sulfonyl halide with the general formula R-SO2-Cl. These compounds react readily with nucleophiles like alcohols and amines (see Hinsberg reaction). If the nucleophile is an alcohol the product is a sulfonic ester, if it is an amine the product is a sulfonamide. Important sulfonic acid chlorides are tosyl chloride, brosyl chloride, nosyl chloride and mesyl chloride. One synthetic procedure to synthesize sulfonic acid chlorides is the Reed reaction. Sulfonyl chloride is very prone to hydrolysis. An ice/water bath can be used to decrease this effect (Titus 1982 & Lefevre 1996).

In popular culture

In the episode "Encyclopedia Galactica" of his TV series Cosmos: A Personal Voyage, Carl Sagan speculates that some intelligent extraterrestrial beings might have a genetic code based on polyaromatic sulfonyl halides instead of DNA.

References

  1. ^ Lehmler HJ (March 2005). "Synthesis of environmentally relevant fluorinated surfactants—a review". Chemosphere 58 (11): 1471–96. doi:10.1016/j.chemosphere.2004.11.078. PMC 2587313. PMID 15694468. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2587313.