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 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 languageEnglish (US)
Pages (from-to)1129-1134
Number of pages6
JournalJournal of Organic Chemistry
Volume59
Issue number5
DOIs
StatePublished - Mar 1 1994

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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