Journal of the American Chemical Society p. 4205 - 4210 (1984)
Update date:2022-08-29
Topics:
Calvo, Kim C.
Westheimer, F. H.
The decomposition of PhCH(PO32-)CHBrCOPh (I) to yield bromide ion, chalcone, and monomeric metaphosphate ion, PO3-, occurs cleanly in methanol at 25 deg C with a rate constant of 69 s-1.Only in the presence of strong base are phosphonic acids fully ionized in methanol, but the reaction is shown to be that of the dianion, and the rate is unaffected by additional nucleophiles.Substitution of a p-methoxyl group into the first phenyl group of I increases the rate about 25-fold and indicates that the formation of the double bond occurs in the rate-limiting step of the overall process; this and additional data rule out the formation of a phostone as intermediate.The reaction thus appears to be a simple fragmentation, where free monomeric metaphosphate is formed.
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