Abstract
In the presence of K 2CO 3, reaction of (2-naphthoyl)methyltriphenylphosphonium bromide ( 1) with methyl 2-perfluoroalkynoates ( 2) in CH 2Cl 2 at room temperature gave methyl 4-(2-naphthoyl)-2-triphenylphosphoranylidene-3-perfluoroalkyl-3-butenoates ( 3) as major products and methyl 4-(2-naphthoyl)-4-triphenylphosphoranylidene-3-perfluoroalkyl-2-butenoates ( 4) as minor products in excellent yields. 4-Perfluoroalkyl-6-(2-naphthyl)-2-pyranones ( 5) were obtained in high yield by hydrolysis of the methylene phosphoranes ( 3) in hot aqueous methanol in a sealed tube. The structures of compounds 3, 4, and 5 were confirmed by IR, MS, 1 H , 19 F and 13 C NMR, and microanalyses. Reaction mechanisms are proposed to account for the formation of products 3, 4, and 5.
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