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Paper | Regular issue | Vol 65, No. 9, 2005, pp.2139-2150
Published online, 22nd July, 2005
DOI: 10.3987/COM-05-10482
Acid Catalyzed Cyclization Reaction of 3-Hydrazono-1,1,1-trifluoro-2-alkanones to 6-Trifluoromethyl-3,6-dihydro-2H-[1,3,4]oxadiazines

Yasuhiro Kamitori* and Tomoko Sekiyama

*Department of Chemical Science and Engineering, Faculty of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan

Abstract

Mechanisms for the acid catalyzed cyclization reaction of 3- dialkylhydrazono-1,1,1-trifluoro-2-alkanones (1) to 6-trifluoromethyl-3,6-dihydro-2H- [1,3,4]oxadiazines (2) are discussed. The results indicate 1,5-sigmatropic shift of hydrogen atom from N-methyl group to carbonyl carbon center on protonated 1 to be a key step for this cyclization reaction.