Abstract Treatment of 1, 1-dimethyl-2-tolylpiperidinium halides with sodium amide in liquid ammonia affords derivatives of 2, 3, 4, 5, 6, 7-hexahydro-1H-2-benzazonine via the Sommelet-Hauser rearrangement. Structures of the reaction products have been established by 13 C nmr. In the case of 1, 1-dimethyl-2-benzylpiperidinium halide, only an elimination reaction takes place.
[Lewis, Frederick D.; Dasharatha Reddy; Schneider, Siegfried; Ga, Michael Journal of the American Chemical Society, 1991 , vol. 113, # 9 p. 3498 - 3506]