Photoreduction of 2-methyl-1-nitro-9,10-anthraquinone in the presence of 1-phenylethanol

doi:10.1039/b811372f

Paper

Photoreduction of 2-methyl-1-nitro-9,10-anthraquinone in the presence of 1-phenylethanol

Published Oct 29, 2008 · H. Gruen, H. Görner

Photochemical & Photobiological Sciences

Q2 SJR score

16

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

The photoreactions of 1-nitro-9,10-anthraquinone ( N1 ) and 2-methyl-1-nitro-9,10-anthraquinone ( N2 ) were studied in benzene and acetonitrile in the presence of 1-phenylethanol. For N2 , a short-lived 10 ns transient observed upon flash photolysis is attributed to a triplet state, which can be intercepted by 1-phenylethanol to form a monohydro radical of N2 and a spectroscopically not detectable donor-derived radical. The decay of radicals yields the corresponding nitroso compound and eventually 1-amino-2-methyl-9,10-anthraquinone ( A2 ) as photoproduct. The final reduction step requires participation of the anthraquinonecarbonyl groups. The yield of radicals and the quantum yield ( Φ _NH_2) of conversion to A2 are small in inert solvents and increase with the donor concentration, approaching Φ _NH_2 = 0.2. No triplet state was observed in the flash photolysis of N1 , but a N1 -derived radical and 1-amino-9,10-anthraquinone ( A1 ) as final products were found. Various mechanistic aspects of complete photoreduction of nitroarenes to aminoarenes are discussed.

Study Snapshot

Photoreduction of 2-methyl-1-nitro-9,10-anthraquinone to 1-amino-2-methyl-9,10-anthraquinone in benzene and acetonitrile in the presence of 1-phenylethanol leads to nitroso compound and 1-a

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Photoreduction of 2-methyl-1-nitro-9,10-anthraquinone in the presence of 1-phenylethanol

Sign up to use Study Snapshot

References

Photochemistry of aromatic nitro compounds, XIII. Photoreduction of sterically hindered nitrobenzenes in aliphatic amines†‡§

Photoreduction of sterically hindered nitrobenzenes in aliphatic amines efficiently produces hydroxylamine derivatives and anilines, with electron transfer mechanism supporting the process.

Syntheses and properties of aromatic nitroso-compounds†

Substituted nitrosobenzenes show visible spectra and a tendency to form dimers, with steric inhibition of resonance playing a role in their formation.

Formal intramolecular photoredox chemistry of anthraquinones in aqueous solution: photodeprotection for alcohols, aldehydes and ketones

Anthraquinones 7-11 can effectively photodeprotect alcohols, aldehydes, and ketones, potentially benefiting photocaging in aqueous solution.

Photoreduction of nitro arenes by formic acid in acetonitrile at room temperature

Formic acid-mediated photoreduction in room temperature acetonitrile solutions provides a clean, versatile, and general method for converting nitro arenes to amines, with wide functional group tolerance and short reaction times.

Magnetic field and methylene chain length effects on photochemistry of bichromophoric chain species containing 7-nitro-2-fluorenyloxy and anilino chromophores

Magnetic field effects significantly affect photochemistry of long-chain bichromophoric compounds, suggesting a different reaction mechanism than short-chain compounds.

Citations