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Rates of reductive elimination of substituted nitrophenols from the (indol-3-yl)methyl position of indolequinones

Abstract:

A series of indolequinones bearing substituted nitrophenols on the (indol-3-yl)methyl position was synthesised. The nitrophenol leaving groups were appropriately substituted to give a wide range (4 units) in phenolic pKa value. The rate of reductive elimination of phenoxide anions from the (indol-3-yl)methyl position of semiquinone radicals was dependent upon this pKa, with a decrease in 3.8 pK units shortening the half-life from 28 to 1.5 ms. Only 2,4-dinitrophenol (pKa = 3.9) was eliminated...

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Publication status:
Published

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Publisher copy:
10.1039/b101842f

Authors


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Institution:
University of Oxford
Department:
Oxford, MSD, Oncology
Naylor, MA More by this author
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Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Issue:
8
Pages:
1340-1345
Publication date:
2001
DOI:
EISSN:
1364-5471
ISSN:
1472-779X
URN:
uuid:568e56fa-9e5c-4374-967d-6ea510de29b9
Source identifiers:
131501
Local pid:
pubs:131501
Language:
English

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