Intramolecular cycloaddition reactions of N-sulfonyl nitrile imides bearing alkenyl groups.
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概要
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The reaction of the <I>p</I>-tolyl(or phenyl)sulfonylhydrazones of some 2-(alkenyloxy)benzaldehydes with lead tetraacetate leads, <I>via</I> the nitrile imide intermediates, Ar–\overset+C=N–\overset−N–SO<SUB>2</SUB>–C<SUB>6</SUB>H<SUB>4</SUB>–X-<I>p</I>, to intramolecular 1,3-dipolar cycloadducts and 1-acetyl-2-aroyl-1-[<I>p</I>-tolyl(or phenyl)sulfonyl]hydrazines in 20–65% and 7–70% yields respectively, while the intermolecular reactions of the benzaldehyde <I>p</I>-tolylsulfonylhydrazone with a dipolarophile such as acrylonitrile or styrene in the presence of lead tetraacetate gives only 1-acetyl-2-benzoyl-1-(<I>p</I>-tolylsulfonyl)hydrazine. The treatment of the <I>N</I>-(<I>p</I>-tolylsulfonyl)-<I>o</I>-(allyloxy)benzohydrazonoyl chloride (<B>10</B>) with triethylamine or by refluxing a benzene solution of <B>10</B> also gives an intramolecular 1,3-dipolar cycloadduct in a good yield.
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