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Communication

A Proposal for the Mechanism-of-Action of Diazoparaquinone Natural Products

Supporting Info

Ken S. Feldman* and Kyle J. Eastman

Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802

J. Am. Chem. Soc., 2005, 127 (44), pp 15344–15345

DOI: 10.1021/ja053880w

Publication Date (Web): October 14, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, ksf@chem.psu.edu

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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Published In Issue November 09, 2005
Received June 13, 2005

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Communication

A Proposal for the Mechanism-of-Action of Diazoparaquinone Natural Products