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■ Computational Study for 1,5-Sigmatropic Hydrogen Shift on Trifluoromethylazadiene Derivatives - The Key Step in the Synthesis of Fluorine-Containing Oxazines -

Norio Ota, Yasuhiro Kamitori,* Takashi Okuda, and Etsuji Okada

*Department of Chemical Science and Engineering, Graduate School of Engineering, Kobe University, 1-1 Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan

Abstract

1,5-Sigmatropic hydrogen shifts on two types of azadiene systems, O-protonated β-trifluoroacetylenamines 9 and 3,3,3-trifluoro-1- alkylideneaminopropen-2-ols 10, are elucidated on the basis of DFT calculations to develop new synthetic methodologies accessing novel fluorine-containing heterocycles. These results suggest that the 1,5-hydrogen shift on 9 and 10 requires slightly further enhanced conditions compared with the corresponding step on diazadiene systems, O-protonated 1,1,1-trifluoro-3-hydrazono-2- alkanones 3, which results in the derivation of oxadiazines 2.