Chemical Behavior of N-Alkyl-N-methylbenzylammonium N-Alkylide

Article abstract of DOI:10.1021/jo00288a057

N-Alkyl-N-methyl(4-substituted benzyl)ammonium N-alkylides (3), produced by fluoride ion induced desilylation of N-alkyl-N-methyl-N-(4-substituted benzyl)-1-(trimethylsilyl)alkylammonium iodides (2), were mainly converted into N-alkyl-N-methyl-1-(4-substituted benzyl)alkylamines (5, Stevens rearrangement products) and 4-substituted toluenes (8).Both compounds were produced via radical-forming and -destroying pathways from 2-substituted-6-<1-(N-alkylmethylamino)alkyl>-5-methylene-1,3-cylohexadienes (4), which were initially formed from 3 by <2,3> sigmatropic rearrangement.There is no direct <1,2> migration pathway from 3 to 5.