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Communication | Regular issue | Vol 12, No. 11, 1979, pp.1453-1456
Published online, 1st January, 1970
DOI: 10.3987/R-1979-11-1453
Thermal Rearrangements of 4- and 6-Vinyl-1,2,5,6-tetrahydropyridine and 2-Vinylpiperidine N-Imides

Takashi Tsuchiya* and Haruki Sashida

*School of Pharmacy, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan

Abstract

The thermolysis of the 4-vinyl-1,2,5,6-tetrahydropyridine N-imide (3) resulted in both [1,2]- and [2,3]-sigmatropic rearrangement to give the diazepine (4) and the pyrazole (5), respectively. This reaction mechanism was confirmed by a deuterium-labelling experiment. Whereas, in the thermolysis of the 2-vinyl derivatives (7 and 12), the [2,3]-rearrangement took place preferentially with the vinyl group to give the ring-expansion products (8 and 13).