Polymers as reagents and catalysts. XI. Stereospecific iodofluorination of alkenes in the presence of polymer supported hydrogen fluoride.

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概要

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• <I>N</I>-Iodosuccinimide reacted with phenyl substituted alkenes in the presence of insoluble polymer supported hydrogen fluoride, which was prepared by reaction of hydrogen fluoride with crosslinked poly(styrene-co-4-vinylpyridine) containing 40–45 mol% of 4-vinylpyridine, thus forming vicinal iodofluorides in high yields. Reactions proceeded with Markovnikov type regioselectivity, and in the case of (<I>Z</I>)- and (<I>E</I>)-stilbene, (<I>Z</I>)- and (<I>E</I>)-1-phenylpropene and indene anti stereospecificity was also observed. Iodofluorinations of phenyl substituted acetylenes occurred regio and stereospecifically, forming (<I>Z</I>)-1-fluoro-2-iodo-1-phenylalkenes, with lower yields than those observed in the case of alkenes.

• 公益社団法人 日本化学会の論文

著者

• Zupan Marko

  "Jo\v{z}ef Stefan" Institute and Department of Chemistry, "E. Kardelj" University

• Gregorcic Ana

  "Jo\v{z}ef Stefan" Institute and Department of Chemistry, "E. Kardelj" University

関連論文

• Polymers as reagents and catalysts. XI. Stereospecific iodofluorination of alkenes in the presence of polymer supported hydrogen fluoride.

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