Intermediate in Sommelet-Hauser Rearrangement of N,N-Dimethylbenzylammonium N-Methylides

Article abstract of DOI:10.1021/jo00296a039

Formation of benzylammonium N-methylides by fluoride anion induced desilylation of dimethyl(4-substituted benzyl)<(trimethylsilyl)methyl>ammonium halides (1) and 3-substituted benzyl analogues (6) was examined to isolate 5-<(dimethylamino)methyl>-6-methylene-1,3-cyclohexadienes (isotoluene intermediates, 3,8,10) in the Sommelet-Hauser rearrangement.Some isotoluenes were isolated and their structures were confirmed by 1H NMR analysis.The stability of the isotoluenes was dependent on the electron-donating effects of the substituents on the conjugated bonds, and 3-methoxy-substituted isotoluene 3a was the most stable compound studied.