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Phenyl vinyl sulfone is used as building blocks in the synthesis of a number of organic substances, participate in polymerization reactions, nucleophilic addition reaction, and in cycloaddition reactions. It is also used in the used in the synthesis of reactive dyes, synthesis of textile fibers, in particular cellulose fibers such as cotton and linen. Other applications in the field of medicine includes as powerful inhibitors of certain enzymatic processes. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dye stuff.
Franklin A. Davis.; Sankar G. Lal.; H. Dupont Durst. Chemistry of oxaziridines. 10. Selective catalytic oxidation of sulfides to sulfoxides using N-sulfonyloxaziridines. J. Org. Chem. 1988, 53, (21), 5004-5007.K Grela .; M Bieniek. Highly selective cross-metathesis with phenyl vinyl sulphone using the 'second generation'Grubbs' catalyst. Tetrahedron Letters. 2001, 42, (36), 6425-6428.
Reactive dienophile. Can function as an acetylene equivalent if benzenesulfinic acid is eliminated thermally from the Diels-Alder adduct to form an olefinic double bond: J. Am. Chem. Soc., 100, 1597 (1978).
Can also behave as an activated form of ethylene if the sulfone group is cleaved from the adduct, e.g. with Na amalgam, with the possibility of prior alkylation of the adduct: J. Org. Chem., 48, 4976 (1983):
For addition to 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, L06100, see: J. Org. Chem., 48, 4986 (1983). Addition to steroids with a cyclopentadienoid D-ring, followed by cleavage of the resulting alkene, gives the diformyl derivatives, useful for further functionalization: J. Chem. Soc., Perkin 1, 241 (1990).
For use in a 1,3-dipolar cycloaddition reaction, see 3-Hydroxypyridine, A13910.
Undergoes the Baylis-Hillman reaction (addition to aldehydes in the presence of 1,4-Diazabicyclo[2.2.2]octane, A14003): Tetrahedron, 44, 6095 (1988).
See also Divinyl sulfone, L12827.
Gefahrenhinweise (EU): H315-H319-H317-H335
Causes skin irritation. Causes serious eye irritation. May cause an allergic skin reaction. May cause respiratory irritation.
Do not get in eyes, on skin, or on clothing. Wear protective gloves. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.