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

doi:10.1021/jo00272a028

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

Chemistry & Biochemistry

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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 language	English (US)
Pages (from-to)	2605-2608
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	54
Issue number	11
DOIs	https://doi.org/10.1021/jo00272a028
State	Published - May 1 1989

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

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.",

author = "Viktor Zhdankin and Michelle Mullikin and Rik Tykwinski and Bruce Berglund and Ronald Caple and Zefirov, {Nikolai S.} and Koz′min, {Anatoly S.}",

year = "1989",

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doi = "10.1021/jo00272a028",

language = "English (US)",

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T1 - Carbon—carbon Bond Formation in Reactions of PhIO •HBF4/Silyl Enol Ether Adduct With Alkenes Or Silyl Enol Ethers

AU - Zhdankin, Viktor

AU - Mullikin, Michelle

AU - Tykwinski, Rik

AU - Berglund, Bruce

AU - Caple, Ronald

AU - Zefirov, Nikolai S.

AU - Koz′min, Anatoly S.

PY - 1989/5/1

Y1 - 1989/5/1

N2 - 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.

AB - 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.

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JF - Journal of Organic Chemistry

IS - 11

ER -

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

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