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Reaction of a-trimethylsilylmethyl-substituted aromatic N-heterocycles with methyl perfluoro(2-methylprop-1-enyl) ether

T. Konakahara, Y. Ono and S. Tamura

Department of Industrial Chemistry, Faculty of Science and Technology, Science University of Tokyo, Noda, Chiba 278, Japan

In order to compare the reactivity of methyl perfluoro(2-methylprop-1-enyl) ether 1 with perfluoro(2-methylpent-2-ene) 2, the reaction of 1 with 2-(trimethylsilylmethyl)pyridines 3 and their analogues was performed. When a mixture of 2-(trimethylsilylmethyl)pyridine 3a and potassium fluoride was treated with 1 in THF, a methylated adduct, 2-[2-methoxy-3,3-bis (trifluoromethyl)but-1-enyl]pyridine 4a, was obtained in 50% yield instead of a cyclized adduct, 2-pentafluoroethyl-3-trifluoromethyl-4H-quinolizin-4-one 5a, which was given from 2.1 However, 2-(trimethylsilylmethyl)quinoline 6a gave an adduct, 2-(4,4,4-trifluoro-2-methoxy-3-trifluoromethylbut-1-enyl) quinoline 7a in 58% yield, accompanied by 23% of the corresponding methylated adduct. The analogous reaction of 2-(trimethylsilylmethyl)benzothiazole is also discussed.

  1. T. Konakahara, T. Murayama, K. Sano and S. Kubota, J. Chem. Res. (M), 1996, 844.


Results and discussion

    Reaction of 2-(trimethylsilylmethyl)prydine (3) with methyl perfluoro(2-methylprop-1-enyl) ether (1)

    Reaction of 2-(trimethylsilylmethyl)quinolines (6) with the ether (1)

    Reaction of 2-(trimethylsilylmethyl)benzothiazole (10) with the ether (1)

    Attempts to cyclize the adduct (11)

    Reaction of the adduct 11 with sodium alkoxides

    Reaction mechanism