Styrylphosphonic dichloride

Styrylphosphonic dichloride has been prepared by the addition of phosphorus pentachloride to styrene with subsequent reaction of the adduct with phosphorus pentoxide or sulfur dioxide. ... 

Sulfinic esters, aromatic, by oxidation of disulfides in alcohols, 46, 64 Sulfonation of D,L-camphor to d,l-10-camphorsulfonic acid, 46,12 Sulfoxides, table of examples of preparation from sulfides with sodium metaperiodate, 46,79 Sulfur dioxide, reaction with styrene phosphorus pentachloride to give styrylphosphonic dichloride, 46,... 

Styrylphosphonic dichloride 60 A solution of styrene (26 g) in benzene (50 ml) is dropped within 30 min, with stirring and exclusion of moisture, into an ice-cooled mixture of phosphorus ) chloride (104 g) and dry benzene (150 ml). The mixture is then stirred for 30 min at room temperature, after which sulfur dioxide is led until the first crystalline product has dissolved, cooling being sometimes necessary at that stage. The benzene is finally removed and the residual liquid is distilled in a vacuum, affording about 90% (about 50 g) of a product, b.p. 107-110o/0.2 mm, that later solidifies (m.p. 71-72°) ... 

A soln. of styrene in dry benzene added during 0.5 hr. under Ng to a stirred ice-cooled mixture of PGI5 and benzene, stirring continued 0.5 hr. at room temp., then SO2 bubbled through the stirred mixture with occasional ice-cooling until the intermediate precipitate is dissolved styrylphosphonic dichloride. Y 8 94%. R. Schmutzler, Org. Synth. 45, 99 (1965). 

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