Cyclization towards Carbon-Carbon Double Bond. III. A New Synthesis of 1-Pyrroline Derivatives and a Synthesis of 1, 2-Dialkyl-3-diphenyl-methlenepyrrolidine Alkyl Halide, an Anti-acetylcholine Substance

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Abstract
2-Substituted 3-diphenylmethylene-1-pyrrolines (III) were synthesized in 1 step by the reaction of 1,1-diphenyl-1,4-butanediol (VII), 2,2-diphenyltetra-hydrofuran (VI), or 4-bromo-1,1-diphenyl-1-butene (V) with nitrile-stannic chloride complex. 2,5-Dimethyl (XI) and 2,5,5-trimethyl-3-diphenylmethylene-1-pyrroline (XII) were obtained respectively from 1,1-diphenyl-1,4-pentanediol (DC) and 1,1-diphenyl-4-methyl-1,4-pentanediol (X). The fact that 2 methyl-3-isopropylidene-1-pyrrollne (XIV) was obtained from 2-methyl-2,5-pentanediol (XB) and 2,2-dimethyltetrahydrofuran (XV) by the same reaction was of interest in contrast with preparation of 1 -pyrrolines (n) by the Ritter reaction. Reduction of the methiodide of m with sodium borohydride gave 1-methyl-2-alkyl-3-diphenylmethylenepyrrolidine. The methiodide of the 2-methyl compound (XVIc) was found to have a comparatively strong anti-acetylcholine activity.

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