Journal of Organic Chemistry p. 2767 - 2770 (1990)
Update date:2022-09-26
Topics:
Shirai, Naohiro
Watanabe, Yoko
Sato, Yoshiro
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.
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