Base induced [1,2]- and [3,2]-rearrangements of N-(2-Thenyl)-N-benzyldimethylammonium ion

The title compound 4 underwent Sommelet and Stevens rearrangements induced by a number of bases. Ionization of the thenyl methylene group of 4 to the corresponding ylid 10 was the prevalent process, yielding subsequently N-2-(2′-thienyl)-2-phenethyl]dimethylamine 12 and N-α-(o-tolyl)-2-thenyl]-dimethylamine 13 . The strong trend of the 2-thenyl ylids to produce large relative amounts of the Sommelet amine was confirmed. Minor products are N-2-(2′-thienyl)-1-phenethyl]dimethylamine 15 and N-α-phenyl-2-(3-methylthienyl)]dimethylamine 16 derived from the benzyl ylid 11 .