Thioamide and thioester cyclopentane synthesis via trimethyltin radical catalyzed alkenylation of substituted (thiocarbonyl)cyclopropanes

Ken S. Feldman, Klaas Schildknegt

Research output: Contribution to journalArticle

11 Citations (Scopus)

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 stereo-chemical outcome of these transformations can be rationalized by considering the effects of substituents upon cyclization of the intermediate functionalized 5-hexenyl radicals.

Original languageEnglish (US)
Pages (from-to)1129-1134
Number of pages6
JournalJournal of Organic Chemistry
Volume59
Issue number5
StatePublished - 1994

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Alkenylation
Bearings (structural)
Cyclopropanes
Thioamides
Cyclopentanes
Gems
Cyclization
trimethyltin

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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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 stereo-chemical 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. / Feldman, Ken S.; Schildknegt, Klaas.

In: Journal of Organic Chemistry, Vol. 59, No. 5, 1994, p. 1129-1134.

Research output: Contribution to journalArticle

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AU - Schildknegt, Klaas

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