Thioamide and Thioester Cyclopentane Synthesis via Trimethyltin Radical Catalyzed Alkenylation of Substituted (Thiocarbonyl)cyclopropanes

Ken S. Feldman; Klaas Schildknegt

doi:10.1021/jo00084a035

Thioamide and Thioester Cyclopentane Synthesis via Trimethyltin Radical Catalyzed Alkenylation of Substituted (Thiocarbonyl)cyclopropanes

Ken S. Feldman, Klaas Schildknegt

Chemistry

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

13 Scopus citations

Abstract

Thioamide cyclopropanes bearing phenyl substituents and thioamide- or thioester cyclopropanes bearing gem-dichloro and methyl substituents were subjected to trimethyltin radical catalyzed alkenylation to furnish the corresponding substituted (thiocarbonyl)cyclopentanes. The stereochemical outcome of these transformations can be rationalized by considering the effects of substituents upon cyclization of the intermediate functionalized 5-hexenyl radicals.

Original language	English (US)
Pages (from-to)	1129-1134
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	59
Issue number	5
DOIs	https://doi.org/10.1021/jo00084a035
State	Published - Mar 1 1994

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo00084a035

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title = "Thioamide and Thioester Cyclopentane Synthesis via Trimethyltin Radical Catalyzed Alkenylation of Substituted (Thiocarbonyl)cyclopropanes",

abstract = "Thioamide cyclopropanes bearing phenyl substituents and thioamide- or thioester cyclopropanes bearing gem-dichloro and methyl substituents were subjected to trimethyltin radical catalyzed alkenylation to furnish the corresponding substituted (thiocarbonyl)cyclopentanes. The stereochemical outcome of these transformations can be rationalized by considering the effects of substituents upon cyclization of the intermediate functionalized 5-hexenyl radicals.",

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AU - Schildknegt, Klaas

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Y1 - 1994/3/1

N2 - Thioamide cyclopropanes bearing phenyl substituents and thioamide- or thioester cyclopropanes bearing gem-dichloro and methyl substituents were subjected to trimethyltin radical catalyzed alkenylation to furnish the corresponding substituted (thiocarbonyl)cyclopentanes. The stereochemical outcome of these transformations can be rationalized by considering the effects of substituents upon cyclization of the intermediate functionalized 5-hexenyl radicals.

AB - Thioamide cyclopropanes bearing phenyl substituents and thioamide- or thioester cyclopropanes bearing gem-dichloro and methyl substituents were subjected to trimethyltin radical catalyzed alkenylation to furnish the corresponding substituted (thiocarbonyl)cyclopentanes. The stereochemical outcome of these transformations can be rationalized by considering the effects of substituents upon cyclization of the intermediate functionalized 5-hexenyl radicals.

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Thioamide and Thioester Cyclopentane Synthesis via Trimethyltin Radical Catalyzed Alkenylation of Substituted (Thiocarbonyl)cyclopropanes

Abstract

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