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

文献情報

出版日 2004-09-14

DOI 10.1039/B408746A

インパクトファクター 6.222

著者

Mami Tojino, Yoshitaka Uenoyama, Takahide Fukuyama, Ilhyong Ryu

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要旨

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-methylene lactams.

掲載誌

Chemical Communications

CiteScore: 8.6

自己引用率: 4.7%

年間論文数: 2458

ChemComm publishes urgent research which is of outstanding significance and interest to experts in the field, while also appealing to the journal’s broad chemistry readership. Our communication format is ideally suited to short, urgent studies that are of such importance that they require accelerated publication. Our scope covers all topics in chemistry, and research at the interface of chemistry and other disciplines (such as materials science, nanoscience, physics, engineering and biology) where there is a significant novelty in the chemistry aspects. Major topic areas covered include: Analytical Chemistry Catalysis Chemical Biology and medicinal chemistry Computational Chemistry and Machine Learning Energy and sustainable chemistry Environmental Chemistry Green Chemistry Inorganic Chemistry Materials Chemistry Nanoscience Organic Chemistry Physical Chemistry Polymer Chemistry Supramolecular Chemistry

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

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