A proposal for the mechanism-of-action of diazoparaquinone natural products

Ken S. Feldman; Kyle J. Eastman

doi:10.1021/ja053880w

A proposal for the mechanism-of-action of diazoparaquinone natural products

Ken S. Feldman, Kyle J. Eastman

Chemistry

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

30 Scopus citations

Abstract

Treatment of the representative diazoparaquinone prekinamycin dimethyl ether with Bu₃SnH/AIBN in aromatic solvents furnishes moderate-to-good yields of formal aryl adducts wherein a molecule of solvent is attached to the carbon (C(11)) previously bearing the diazo function. Substituent studies provide evidence in support of a radical aromatic substitution mechanism, in which radical addition to the diazoparaquinone function generates an intermediate C(11) vinylic radical.

Original language	English (US)
Pages (from-to)	15344-15345
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	44
DOIs	https://doi.org/10.1021/ja053880w
State	Published - Nov 9 2005

All Science Journal Classification (ASJC) codes

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja053880w

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abstract = "Treatment of the representative diazoparaquinone prekinamycin dimethyl ether with Bu3SnH/AIBN in aromatic solvents furnishes moderate-to-good yields of formal aryl adducts wherein a molecule of solvent is attached to the carbon (C(11)) previously bearing the diazo function. Substituent studies provide evidence in support of a radical aromatic substitution mechanism, in which radical addition to the diazoparaquinone function generates an intermediate C(11) vinylic radical.",

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AB - Treatment of the representative diazoparaquinone prekinamycin dimethyl ether with Bu3SnH/AIBN in aromatic solvents furnishes moderate-to-good yields of formal aryl adducts wherein a molecule of solvent is attached to the carbon (C(11)) previously bearing the diazo function. Substituent studies provide evidence in support of a radical aromatic substitution mechanism, in which radical addition to the diazoparaquinone function generates an intermediate C(11) vinylic radical.

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A proposal for the mechanism-of-action of diazoparaquinone natural products

Abstract

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