A new method for the generation and cyclization of iminyl radicals via the Hudson reaction

Xichen Lin; Didier Stien; Steven M. Weinreb

doi:10.1021/ol990720e

A new method for the generation and cyclization of iminyl radicals via the Hudson reaction

Xichen Lin
, Didier Stien
, Steven M. Weinreb

Chemistry

Research output: Contribution to journal › Article › peer-review

58 Scopus citations

Abstract

(Matrix presented) A mild new synthetic procedure has been developed for in situ generation and cyclization of iminyl radicals onto pendant alkenes, followed by functionalization of the resulting carbon radical by one of a variety of trapping reagents. The key process in the method involves production of the iminyl radical via treatment of an aldoxime or ketoxime with readily available 2,6-dimethylbenzenesulfinyl chloride at -50°C to room temperature (Hudson reaction).

Original language	English (US)
Pages (from-to)	637-639
Number of pages	3
Journal	Organic Letters
Volume	1
Issue number	4
DOIs	https://doi.org/10.1021/ol990720e
State	Published - Aug 26 1999

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol990720e

Cite this

@article{b6143fd36ef143d1a4bfade2dc7359a4,

title = "A new method for the generation and cyclization of iminyl radicals via the Hudson reaction",

abstract = "(Matrix presented) A mild new synthetic procedure has been developed for in situ generation and cyclization of iminyl radicals onto pendant alkenes, followed by functionalization of the resulting carbon radical by one of a variety of trapping reagents. The key process in the method involves production of the iminyl radical via treatment of an aldoxime or ketoxime with readily available 2,6-dimethylbenzenesulfinyl chloride at -50°C to room temperature (Hudson reaction).",

author = "Xichen Lin and Didier Stien and Weinreb, \{Steven M.\}",

year = "1999",

month = aug,

day = "26",

doi = "10.1021/ol990720e",

language = "English (US)",

volume = "1",

pages = "637--639",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "4",

}

TY - JOUR

T1 - A new method for the generation and cyclization of iminyl radicals via the Hudson reaction

AU - Lin, Xichen

AU - Stien, Didier

AU - Weinreb, Steven M.

PY - 1999/8/26

Y1 - 1999/8/26

N2 - (Matrix presented) A mild new synthetic procedure has been developed for in situ generation and cyclization of iminyl radicals onto pendant alkenes, followed by functionalization of the resulting carbon radical by one of a variety of trapping reagents. The key process in the method involves production of the iminyl radical via treatment of an aldoxime or ketoxime with readily available 2,6-dimethylbenzenesulfinyl chloride at -50°C to room temperature (Hudson reaction).

AB - (Matrix presented) A mild new synthetic procedure has been developed for in situ generation and cyclization of iminyl radicals onto pendant alkenes, followed by functionalization of the resulting carbon radical by one of a variety of trapping reagents. The key process in the method involves production of the iminyl radical via treatment of an aldoxime or ketoxime with readily available 2,6-dimethylbenzenesulfinyl chloride at -50°C to room temperature (Hudson reaction).

UR - https://www.scopus.com/pages/publications/0033606858

UR - https://www.scopus.com/pages/publications/0033606858#tab=citedBy

U2 - 10.1021/ol990720e

DO - 10.1021/ol990720e

M3 - Article

C2 - 10823192

AN - SCOPUS:0033606858

SN - 1523-7060

VL - 1

SP - 637

EP - 639

JO - Organic Letters

JF - Organic Letters

IS - 4

ER -

A new method for the generation and cyclization of iminyl radicals via the Hudson reaction

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this