Tributylphosphonium chlorides

A suspension of nutshell particles in DMF was quatemized with tributyl-phosphine. This converted the encapsulated poly(VBC) into poly[(vinylben-zyl)-tributylphosphonium chloride]. The EDS experiments indicated a low surface concentration of phosphorus in the quaternized samples. Since the elemental analysis indicated a high content of phosphorus in all the samples, one can infer that the quaternary onium cations are hidden inside the polystyrene cages . 

Ketone syntheses. Aeyl derivatives du beyond the first round include A-ac>l tributylphosphonium chlorides (generated in n olving )V-methoxy-(V-methyl carboxamide ct-chloro ketones, a-keto amides, and a-diket Svmmetrical diketones are obtained by th -nethiodides. Note that an analogous reactia rumishes aldehydes. ... 

The single recently published application of the amide form was in the synthesis of the histone deacetylase inhibitor vorinostat (1691 (Figure 6.52). Phosphonium salt 166 was prepared by the reaction of triphenylphosphine with chloro[l- C]acetanilide, itself prepared via chloro [l- " C]acetyl chloride. Olefination of aldehyde 167 with the yhde produced from 166 furnished the a,/3-unsaturated amide 168 in 85% yield °. The tributylphosphonium analog was employed as a starting material for the synthesis of [ " C]GV 1550526, a glutamate co-agonist . 

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