The reactions of 1,1-disubstituted ethenes with barbituric acid and its derivatives in the presence of manganese(II) acetate and air yielded 5,5-bis(2-hydroperoxyalkyl)barbituric acids 3aa-ac and 3ba-ja in 62-99% yields. The structure of 3ab was determined by X-ray crystallography. The reaction of la and 2a was also effected by manganese(III) acetate (95%) and metallic manganese (92%), but in poor yield by cerium(IV) ammonium nitrate (50%). Treatment of 5,5-bis(2-hydroperoxy-2.2-diphenylethyl)-l,3-dimethylbarbituric acid (3aa) with perchloric acid gave 5,5-bis(benzoylmethyl)-1.3-dimethylbarbituric acid ( 6) and 5-(2-benzoylmethyl)-l,3-dimethyl-5-(2,2-diphenylethenyl)barbituric acid (7), in which phenyl migration took place. Reduction of 3aa with zinc powder in acetic acid or with triphenylphosphine in diethyl ether yielded 5,5-bis(2-hydroxy-2,2-diphenylethyI)-1.3-dimethylbarbituric acid (10), which was dehydrated to give a spirotetrahydropyran 11.
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