Tetrahedron p. 433 - 442 (1983)
Update date:2022-08-16
Topics:
Julia, M.
Mestdagh, H.
O-Alkylation of amides and ureas was easily accomplished with alkyldiphenylsulphonium salts.These alkylating agents are readily available, often crystalline, and non-hygroscopic.They are somewhat less powerful than oxonium salts but are not limited to methyl and ethyl groups.The following order of reactivities was observed: PhCH2S(+)Ph2<*>EtS(+)Ph2<*>Et2SO4<*>MeS(+)Ph2.Benzylation proceeded under very mild conditions (room temperature).The counterion and solvent have no significant influence on the reaction rate.Sulphonium salts where the leaving group is a dialkyl sulphide are much less active as alkylating agents.New alkoxymethyleneiminium salts have been prepared in this way in yields above 70 percent.
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