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

Mami Tojino; Yoshitaka Uenoyama; Takahide Fukuyama; Ilhyong Ryu

doi:10.1039/b408746a

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

Department of Applied Chemistry

Research output: Contribution to journal › Article › peer-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 language	English
Pages (from-to)	2482-2483
Number of pages	2
Journal	Chemical Communications
Volume	10
Issue number	21
DOIs	https://doi.org/10.1039/b408746a
State	Published - 7 Nov 2004

Access to Document

10.1039/b408746a

Fingerprint Dive into the research topics of 'Intramolecular nucleophilic carbonyl trapping of α-ketenyl radicals by an amino group'. Together they form a unique fingerprint.

Cite this

@article{edafb9468e4947c8bfb631679353d297,

title = "Intramolecular nucleophilic carbonyl trapping of α-ketenyl radicals by an amino group",

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.",

author = "Mami Tojino and Yoshitaka Uenoyama and Takahide Fukuyama and Ilhyong Ryu",

year = "2004",

month = nov,

day = "7",

doi = "10.1039/b408746a",

language = "English",

volume = "10",

pages = "2482--2483",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "21",

}

TY - JOUR

T1 - Intramolecular nucleophilic carbonyl trapping of α-ketenyl radicals by an amino group

AU - Tojino, Mami

AU - Uenoyama, Yoshitaka

AU - Fukuyama, Takahide

AU - Ryu, Ilhyong

PY - 2004/11/7

Y1 - 2004/11/7

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=9444291899&partnerID=8YFLogxK

U2 - 10.1039/b408746a

DO - 10.1039/b408746a

M3 - Article

C2 - 15514826

AN - SCOPUS:9444291899

VL - 10

SP - 2482

EP - 2483

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 21

ER -

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

Abstract

Access to Document

Other files and links

Cite this