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Paper | Regular issue | Vol 45, No. 12, 1997, pp.2357-2364
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7943
Addition of Propargyltrimethylsilane to N-Methyleneamine Equivalents: Generation and Electrophilic Cyclization of Vinylic Carbocations

Hyun-Joon Ha,* Young-Seong Lee, and Young-Gil Ahn

*Department of Chemistry, Hankuk University of Foreign Studies, Yongin, Kyunggi-Do, 449-791, Korea

Abstract

Lewis acid induced N-methyleneamine equivalents from N-(methoxymethyl)anilines or 1,3,5-triphenylhexahydro-1,3,5-triazines reacted with propargyltrimethylsilanes to give N-buta-2,3-dienylanilines, 4-methylene-1,2,3,4-tetrahydroquinolines and its oxidized product of 4-methylquinolines. These products came from branching reactions of the elimination and electrophilic aromatic substitution from the same vinylic carbocation intermediate.