Titanium dioxide photocatalysed alkylation of maleic acid derivatives

Article abstract of DOI:10.1016/S0040-4020(98)00020-9

The irradiation of a nitrogen-flushed acetonitrile suspension of titanium dioxide in the presence of benzyltrimethylsilane, its 4-methoxy derivative or 4-methoxyphenylacetic acid as the donors and maleic acid, maleic anhydride or related nitriles as the accepters leads to the corresponding benzylsuccinic acid derivatives via electron, hole transfer and fragmentation of the benzyl radical cation (such a cleavage is too slow with 4-methoxytoluene). A rationale of the reaction and an evaluation of the synthetic significance of the method are given.