2222-30-2Relevant academic research and scientific papers
Reductive photocarboxylation of phenantnrene: A mechanistic investigation
Nikolaitchik, Alexander V.,Rodgers, Michael A. J.,Neckers, Douglas C.
, p. 1065 - 1072 (2007/10/03)
Irradiation of a solution of phenanthrene (PHN) in DMSO saturated with CO2 in the presence of N,N-dimethylaniline (DMA) produced 9,10-dihydrophenanthrene-9-carboxylic acid (1) in 55% yield, trans-9,10-dihydrophenanthrene-9,10-dicarboxylic acid (2) in 11% yield, a trace of phenanthrene-9-carboxylic acid (3), and a trace of 10-[p-(N,N-dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylic acid (5). Addition of cumene, a hydrogen donor, or water, a proton donor, decreased the yield of 2, while addition of certain salts increased its yield. 9-Carboxy-9,10-dihydrophenanthr-10-yl, generated by irradiation of phenanthrene-9-carboxylic acid in the presence of DMA, is proposed to be an intermediate in the formation of the acids. The quantum yield for the formation of 2 increased to a maximum of 0.13 with increasing light intensity. High CO2 concentrations in DMSO changed the reaction pathway, greatly reducing the yields of 1 and 2, and phenanthrene-9-carboxylic acid (3) and 10-[p-(N,N-dimethylamino)phenyl]-9,10-dihydrophenanthrene-9-carboxylic acid (5) were formed instead. On the basis of these results reduction of 9-carboxy-9,10-dihydrophenanthr-10-yl with the phenanthrene radical anion is proposed to be a step in the mechanism accounting for trans-9,10-dihydrophenanthrene-9,10-dicarboxylic acid formation. Transient spectroscopic evidence in support of this proposal is presented.
Reductive Photocarboxylation of Aromatic Hydrocarbons
Tazuke, Shigeo,Kazama, Shingo,Kitamura, Noboru
, p. 4548 - 4553 (2007/10/02)
Photoirradiation of aromatic hydrocarbons such as phenanthrene, anthracene, or pyrene in the presence of an amine and carbon dioxide in dipolar aprotic solvents resulted in reductive carboxylation of the hydrocarbon.The reaction was considered to proceed
