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Sulfonic and Phosphonic Acids Formed by Bisulfite and Phosphite Adduct Formation with Pyrimidinones
Benneche, Tore,Strande, Per,Undheim, Kjell
, p. 448 - 454 (2007/10/02)
By analogy with carbonyl compounds, ?-electron deficient 2-pyrimidinones form adducts with sodium bisulfite and phosphite esters.Both the 3,4- and 3,6-bisulfite adducts were found.The 3,4-isomer was often predominant and was obtained isomerically pure by selective precipitation from an aqueous solution.The adduct formation is reversible in aqueous solution.The adduct was also readily cleaved by trifluoroacetic acid.With tris(trimethylsilyl) phosphite, regiospecific formation of the 3,4-adduct was observed.The corresponding 3,4-dihydro-4-phosphonic acid was prepared by methanol cleavage of the silyl ester function.
