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Trifluoroaceto-N-phenylhydrazonoyl halides, the precursors of trifluoroacetonitrile phenylimine, prepared by halogenation of trifluoroacetaldehyde phenylhydrazone, react with various olefins and acetylenes in the presence of triethylamine to give 3-trifluoromethylpyrazolines and pyrazoles, respectively. The regioselective results are discussed in terms of HOMO-LUMO interaction of trifluoroacetonitrile phenylimine and dipolarophiles.
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Tanaka et al. (1982) studied this question.
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