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2005
Ring closure reactions
O 0130
Intramolecular Nucleophilic Carbonyl Trapping of α-Ketenyl Radicals by an
Amino Group. — Free-radical carbonylation of ω-alkynylamines with tributyltin hy14- 037 dride
(III) gives a mixture of α-methylene lactams (V) and α-stannyl lactams (IV). Nucleophilic addition of the 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 (V). — (TOJINO, M.; UENOYAMA, Y.; FUKUYAMA, T.;
RYU*, I.; Chem. Commun. (Cambridge) 2004, 21, 2482-2483; Dep. Chem., Fac. Arts
Sci., Osaka Prefect. Univ., Osaka 599, Japan; Eng.) — M. Paetzel
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