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Oxidation of Polynuclear Aromatic Hydrocarbons using Ruthenium‐Ion‐Catalyzed Oxidation: The Role of Aromatic Ring Number in Reaction Kinetics and Product Distribution
Author(s) -
Nowicka Ewa,
Clarke Tomos J.,
Sankar Meenakshisundaram,
Jenkins Robert L.,
Knight David W.,
Golunski Stanislaw,
Hutchings Graham J.,
Willock David J.,
Francisco Manuel,
Taylor Stuart H.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201704133
Subject(s) - aromaticity , chemistry , product distribution , aromatic hydrocarbon , solvent , ruthenium , catalysis , molecule , ring (chemistry) , photochemistry , hydrocarbon , organic chemistry
Oxidation of aromatic hydrocarbons with differing numbers of fused aromatic rings (2–5), have been studied in two solvent environments (monophasic and biphasic) using ruthenium‐ion‐catalyzed oxidation (RICO). RICO reduces the aromaticity of the polyaromatic core of the molecule in a controlled manner by selective oxidative ring opening. Moreover, the nature of the solvent system determines the product type and distribution, for molecules with more than two aromatic rings. Competitive oxidation between substrates with different numbers of aromatic rings has been studied in detail. It was found that the rate of polyaromatic hydrocarbon oxidation increases with the number of fused aromatic rings. A similar trend was also identified for alkylated aromatic hydrocarbons. The proof‐of‐concept investigation provides new insight into selective oxidation chemistry for upgrading of polyaromatic molecules.