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1986•Angewandte Chemie International Edition in EnglishRequires access

Poly‐Onio‐Substituted Quinones as Strong Electron Acceptors

Robert Weiß, Norbert J. Salomon, Georg E. Miess, Reinhard Roth

Open publisher page 34 citations

Abstract

The bis- and tetrakispyridino-substituted quinones 1 and 2 are stronger oxidizing agents than the known neutral systems p-chloranil 3 and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The first reduction potential of 2 is + 0.73 V (vs. Ag/AgCl)! The new oxidizing agents 1 and 2 are also interesting preparatively, because they are readily obtainable from p-chloranil 3 and the transmaination reagent 4 and are insoluble in conventional aprotic solvents for all oxidation stages (which permits simple workup).

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What this paper is about

The bis- and tetrakispyridino-substituted quinones 1 and 2 are stronger oxidizing agents than the known neutral systems p-chloranil 3 and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The first reduction potential of 2 is + 0.73 V (vs. Ag/AgCl)! The new oxidizing agents 1 and 2 are also interesting preparatively, because they are readily obtainable from p-chloranil 3 and the transmaination reagent 4 and are insoluble in conventional aprotic solvents for all oxidation stages (which permits simple workup).

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Available abstract

The bis- and tetrakispyridino-substituted quinones 1 and 2 are stronger oxidizing agents than the known neutral systems p-chloranil 3 and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ). The first reduction potential of 2 is + 0.73 V (vs. Ag/AgCl)! The new oxidizing agents 1 and 2 are also interesting preparatively, because they are readily obtainable from p-chloranil 3 and the transmaination reagent 4 and are insoluble in conventional aprotic solvents for all oxidation stages (which permits simple workup).

Key concepts: Chloranil, Oxidizing agent, Reagent, Chemistry, Benzoquinone, Electron acceptor, Photochemistry, Organic chemistry

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