Carbon—carbon Bond Formation in Reactions of PhIO •HBF4/Silyl Enol Ether Adduct With Alkenes Or Silyl Enol Ethers

Viktor Zhdankin, Michelle Mullikin, Rik Tykwinski, Bruce Berglund, Ronald Caple, Nikolai S. Zefirov, Anatoly S. Koz′min

Research output: Contribution to journalArticle

60 Scopus citations

Abstract

A new method for generation of reactive α-ketomethyl aryliodonium intermediates from silyl enol ethers and PhIO.HBF4has been developed. Reactions of PhIO-HBF4/silyl enol ether adduct with alkenes (1-hexene, cyclohexene, a-methylstyrene, allyltrimethylsilane, 2,3-dimethyl-2-butene) yielded products of allylic alkylation or (in case of 2,3-dimethyl-2-butene) a substituted dihydrofuran. Reactions of adducts from PhIO/HBF4and silyl enol ethers of acetophone, p-chloroacetophenone, p-methylacetophenone, and p-nitroacetophenone with various silyl enol ethers led to unsymmetrical 1,4-butanediones as major products.

Original languageEnglish (US)
Pages (from-to)2605-2608
Number of pages4
JournalJournal of Organic Chemistry
Volume54
Issue number11
DOIs
StatePublished - May 1 1989

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