Styrene hydroxylation, stereoselective

Preparation of Phosphines by Addition of P-H to Unsaturated Compounds. -This route has not received much attention over the past year. A stereoselective synthesis of tris(Z-styryl)phosphine is offered by the addition of phosphine to phenylacetylene in a superbasic system (HMPA-H20-K0H)." In a similar vein, the reaction of phosphine with styrene and a-methylstyrene in a superbasic medium (DMSO-KOH) provides a route to the primary phosphines, (2-phenylethyl)phosphine and (2-methyl-2-phenylethyl)phosphine, respectively. 7 Transition metal phosphine complexes have been shown to catalyse the a-hydroxylation, P-cyanoethylation, and P-alkoxycarbonylethylation of phosphine. 71 Addition of primary phosphines to acrylic esters has been used for the synthesis of the phosphines (80).7 A similar addition of diphenylphosphine to acrylic esters and amides has given a series of hydrophilic phosphines (81). 72 The bis(phosphorinanyl)ethane (82) is formed in the photochemical addition of l,2-bis(phosphino)ethane to 1,4-pentadiene. ... 

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