Journal of Organic Chemistry p. 2605 - 2608 (1989)
Update date:2022-08-04
Topics:
Zhdankin, Viktor V.
Mullikin, Michelle
Tykwinski, Rik
Berglund, Bruce
Caple, Ronald
et al.
A new method for generation of reactive α-ketomethyl aryliodonium intermediates from silyl enol ethers and PhIO*HBF4 has been developed.Reactions of PhIO*HBF4/silyl enol ether adduct with alkenes (1-hexene, cyclohexene, α-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/HBF4 and 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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