Abstract
Photoreduction of o-benzoquinones in the presence of p-bromo-N,N-dimethylaniline under irradiation (λ > 500 nm) affords the corresponding pyrocatechols and hydroxyphenyl ethers. The latter are unstable and, in turn, decompose in the dark reaction to pyrocatechols. The ratio between pyrocatechol and hydroxyphenyl ether formed upon the photoreaction is determined by the structure of o-quinone, namely, the presence and bulk of substituents in positions 3 and 6 of the ring. The yield of pyrocatechol is maximal (60—65%) if the substituents are the same (H and H, But and But) or insignificantly differ (Pri and But), regardless of its bulk.
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Chesnokov, S.A., Cherkasov, V.K., Abakumov, G.A. et al. Photoreduction of o-benzoquinones in the presence of p-bromo-N,N-dimethylaniline. Russian Chemical Bulletin 52, 718–724 (2003). https://doi.org/10.1023/A:1023931428206
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DOI: https://doi.org/10.1023/A:1023931428206