Intramolecular carbozincation of unactivated alkenes occurs through a zinc radical transfer mechanism.

Intramolecular carbozincation of unactivated alkenes occurs through a zinc radical transfer mechanism. Research Abstract Details 

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Intramolecular carbozincation of unactivated alkenes occurs through a zinc radical transfer mechanism. Abstract Text:

Theodore Cohen,Heather Gibney,Roman Ivanov,Edmund A-H Yeh,Ilan Marek,Dennis P Curran,Theodore Cohen,Heather Gibney,Roman Ivanov,Edmund A-H Yeh,Ilan Marek,Dennis P Curran,

The cyclizations of a number of terminally unsaturated alkenyl zinc iodides to cyclopentylmethylzinc iodides, formerly believed to be nonradical in nature, have been revealed as radical chain cyclizations initiated by adventitious oxygen. Five cases are presented in which the published carbozincation cis/trans selectivities are essentially the same as those found for the cyclizations of the unsaturated alkyl iodide precursors of the alkylzinc iodides by the iodine atom transfer method at approximately the same temperatures. In addition, it has been found that one of the organozinc cyclizations does not occur in a system in which oxygen has been rigorously excluded. The combined findings strongly suggest that these organozinc cyclizations occur by a zinc radical transfer mechanism rather than by a conventional carbometallation that is thought to occur with the analogous organolithium and organomagnesium cyclizations.

Intramolecular carbozincation of unactivated alkenes occurs through a zinc radical transfer mechanism. Publishing Authors By Initials

T Cohen,H Gibney,R Ivanov,EA Yeh,I Marek,DP Curran,T Cohen,H Gibney,R Ivanov,EA Yeh,I Marek,DP Curran,

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Intramolecular carbozincation of unactivated alkenes occurs through a zinc radical transfer mechanism. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of the American Chemical Society

VOLUME: 129

Page Numbers: 15405-9

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 1520-5126

DAY: 8

MONTH: 11

YEAR: 2007

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LANGUAGE: eng

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Grant and Affiliation Information for Intramolecular carbozincation of unactivated alkenes occurs through a zinc radical transfer mechanism.

AFFILIATION: Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. cohen@pitt.edu

Country: United States

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MEDLINETA: J Am Chem Soc

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