On the mechanism of the intramolecular samarium barbier reaction. Probes for formation of radical and organosamarium intermediates

Dennis P. Curran; Xin Gu; Wei Zhang; Paul Dowd

doi:10.1016/S0040-4020(97)00608-X

On the mechanism of the intramolecular samarium barbier reaction. Probes for formation of radical and organosamarium intermediates

Dennis P. Curran
, Xin Gu
, Wei Zhang
, Paul Dowd

Chemistry

University of Pittsburgh

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

Abstract

A new type of mechanistic probe for the intramolecular samarium Barbier reaction has been designed, and two different probe substrates have been investigated in detail. Remarkably, no unambiguous evidence could be obtained in favor of any of the obvious intermediates (free alkyl or alkoxy radicals, ketyls, organosamarium species) that are postulated for this reaction. Several possibilities for modified mechanisms are suggested.

Original language	English
Pages (from-to)	9023-9042
Number of pages	20
Journal	Tetrahedron
Volume	53
Issue number	27
DOIs	https://doi.org/10.1016/S0040-4020(97)00608-X
State	Published - Jul 7 1997

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4020(97)00608-X

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abstract = "A new type of mechanistic probe for the intramolecular samarium Barbier reaction has been designed, and two different probe substrates have been investigated in detail. Remarkably, no unambiguous evidence could be obtained in favor of any of the obvious intermediates (free alkyl or alkoxy radicals, ketyls, organosamarium species) that are postulated for this reaction. Several possibilities for modified mechanisms are suggested.",

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On the mechanism of the intramolecular samarium barbier reaction. Probes for formation of radical and organosamarium intermediates

Abstract

ASJC Scopus Subject Areas

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