Journal of Organic Chemistry p. 334 - 337 (1990)
Update date:2022-09-26
Topics:
Okazaki, Seiji
Shirai, Naohiro
Sato, Yoshiro
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.
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