By R J Cremlyn
Considering that its discovery in 1854, chlorosulfonic acid has validated that it's a really flexible reagent. it truly is typical as a sulfonating and chlorosulfonating agent, relatively of natural compounds, and it presents priceless artificial intermediates for plenty of branches of undefined. This booklet presents an in depth, modern account of the reactions of chlorosulfonic acid with aliphatic, fragrant and heterocyclic compounds; reactions with components and inorganic compounds also are mentioned, besides using the reagent as a robust acid catalyst and dehydrating agent. ultimately, the economic makes use of and manufacture of chlorosulfonic acid are reviewed. The specified assurance during this e-book, coupled with the various references to contemporary paintings, will make sure that it really is welcomed as a reference by means of man made chemists in, for instance, the pharmaceutical, agrochemical, plastic and detergent industries. Researchers and their scholars in academia also will locate it a invaluable addition to their bookshelves.
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Extra resources for Chlorosulfonic acid: a versatile reagent
Olivella, ‘Aromatic and Alkaromatic Chlorocarbons’ in Polychloroaromatic Compounds, H. Suschitzky, (ed), Plenum Press, London, 1974, 6. J. N. Cronje, Phosphorus and Sulfur, 1979,6, 495. H. H. Carten, J ; Am. Chem. ,1940,62, 51 1,603. H. S. Authenrieth, J Am. Chem. ,1941, 63, 3446. 51 A. Newton, J ; Am. Chem. ,1943,65,2439. 52 M . P. Rieck, Chem. , 1976, 100,391; Chem. , 85, 159332. 53 S. H. Richter, J Am. Chem. ,1949,71,453. CHAPTER 3 Reactions of Organic Sulfortyl Chlorides 1 Reactions with Nucleophilic Reagents As mentioned in Chapter 2, chlorosulfonic acid is a valuable reagent for the conversion of organic compounds into their sulfonyl chlorides.
01 M KC1) involves the sulfenes 15 and 1634(Equation 13). Me$3--CH2SO2CI 14 H20 (KCI) [CH2=S02] + [ Me3SiCH=S02] 15 16 (13) More recent experiments by King and c o - ~ o r k e r sstudied ~ ~ the hydrolysis of other alkylsulfonyl chlorides, including 2,2,2-trifluoroethyl- and tertiary butyl-sulfonyl chlorides. g. halogens) and electron-accepting substituents at the a-carbon atom of alkylsulfonyl halides; (b) the use of catalysts with Chapter 3 26 pronounced basic properties; and (c) the use of a polar reaction m e d i ~ m .
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Chlorosulfonic acid: a versatile reagent by R J Cremlyn