Ketene Thioacetal Route to γ-Lactones. Effect of Carbonyl Hardness on Reaction-Site Selectivity and a Unique Preparation of 3-Methyl-5-phenyl-2(5H)-furanone

Alan P. Kozikowski; Yon Yih Chen

doi:10.1021/jo01299a039

Ketene Thioacetal Route to γ-Lactones. Effect of Carbonyl Hardness on Reaction-Site Selectivity and a Unique Preparation of 3-Methyl-5-phenyl-2(5H)-furanone

Alan P. Kozikowski, Yon Yih Chen

School of Medicine

Research output: Contribution to journal › Article › peer-review

34 Scopus citations

Abstract

The synthesis of γ-lactones from the addition products of ketene thioacetal anions and carbonyl compounds has been achieved. A unique phenylselenenyl chloride triggered formation of dithienium ion from ketene thioacetal has been shown to directly afford a doubly protected butenolide system.

Original language	English (US)
Pages (from-to)	2236-2239
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	45
Issue number	11
DOIs	https://doi.org/10.1021/jo01299a039
State	Published - Jan 1 1980

ASJC Scopus subject areas

Organic Chemistry

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abstract = "The synthesis of γ-lactones from the addition products of ketene thioacetal anions and carbonyl compounds has been achieved. A unique phenylselenenyl chloride triggered formation of dithienium ion from ketene thioacetal has been shown to directly afford a doubly protected butenolide system.",

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N2 - The synthesis of γ-lactones from the addition products of ketene thioacetal anions and carbonyl compounds has been achieved. A unique phenylselenenyl chloride triggered formation of dithienium ion from ketene thioacetal has been shown to directly afford a doubly protected butenolide system.

AB - The synthesis of γ-lactones from the addition products of ketene thioacetal anions and carbonyl compounds has been achieved. A unique phenylselenenyl chloride triggered formation of dithienium ion from ketene thioacetal has been shown to directly afford a doubly protected butenolide system.

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Ketene Thioacetal Route to γ-Lactones. Effect of Carbonyl Hardness on Reaction-Site Selectivity and a Unique Preparation of 3-Methyl-5-phenyl-2(5H)-furanone

Abstract

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