Intramolecular nucleophilic carbonyl trapping of α-ketenyl radicals by an amino group

Mami Tojino, Yoshitaka Uenoyama, Takahide Fukuyama, Ilhyong Ryu*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

42 Scopus citations

Abstract

Free-radical carbonylation of ω-alkynylamines with tributyltin hydride gives a mixture of α-methylene lactams and α- stannylmethylene lactams. Nucleophilic addition of an internal amino group to the carbonyl group of α-ketenyl radicals is proposed as the cyclization step. The subsequent unusual 1,4-H shift from the resulting 1-hydroxyallyl radical, followed by elimination of the β-tributyltin radical leads to the formation of α-methy lene lactams.

Original languageEnglish
Pages (from-to)2482-2483
Number of pages2
JournalChemical Communications
Volume10
Issue number21
DOIs
StatePublished - 7 Nov 2004

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