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

Access to Document

10.1021/ja053880w

Cite this

@article{1979376dd39e4e9391235731a7733b08,

title = "A proposal for the mechanism-of-action of diazoparaquinone natural products",

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.",

author = "Feldman, \{Ken S.\} and Eastman, \{Kyle J.\}",

year = "2005",

month = nov,

day = "9",

doi = "10.1021/ja053880w",

language = "English (US)",

volume = "127",

pages = "15344--15345",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

number = "44",

}

TY - JOUR

T1 - A proposal for the mechanism-of-action of diazoparaquinone natural products

AU - Feldman, Ken S.

AU - Eastman, Kyle J.

PY - 2005/11/9

Y1 - 2005/11/9

N2 - 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.

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.

UR - https://www.scopus.com/pages/publications/27644487203

UR - https://www.scopus.com/pages/publications/27644487203#tab=citedBy

U2 - 10.1021/ja053880w

DO - 10.1021/ja053880w

M3 - Article

C2 - 16262378

AN - SCOPUS:27644487203

SN - 0002-7863

VL - 127

SP - 15344

EP - 15345

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 44

ER -

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

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this