- Reductive photocarboxylation of phenantnrene: A mechanistic investigation
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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.
- Nikolaitchik, Alexander V.,Rodgers, Michael A. J.,Neckers, Douglas C.
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p. 1065 - 1072
(2007/10/03)
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- The Baeyer-Villiger Reaction of Polycyclic Aromatic Aldehydes: Preparation of Polycyclic Phenols
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Baeyer-Villiger reactions of such polycyclic aromatic aldehydes as 2-dibenzofurancarbaldehyde with various peroxy compounds have been studied in detail, giving predominantly the corresponding phenols.
- Fujishiro, Koichi,Mitamura, Shuichi
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p. 4464 - 4466
(2007/10/02)
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- PHOTOCATALYSIS OF THE PSCHORR REACTION BY TRIS-(2,2'-BIPYRIDYL)RUTHENIUM(II) IN THE PHENANTHRENE SERIES
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The photocatalytic conversion of the tetrafluoroborate salt of the stilbenediazonium ion (1) into the corresponding phenanthrene (2) (Pschorr reaction) by Ru(bpy)3(2+) (bpy = 2,2'-bipyridyl) has been investigated.We have shown that this particular Pshorr
- Cano-Yelo, Herminia,Deronzier, Alain
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p. 1093 - 1098
(2007/10/02)
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- Reactions of Halogenated α-Phenylcinnamic Acids with Potassium Amide in Liquid Ammonia : Part I - Reactions of cis- and trans-2-Chloro-α-phenylcinnamic Acids
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Reaction of trans- and cis-2-chloro-α-phenylcinnamic acids (1) with KNH2 in liquid ammonia gives phenanthrene-9-carboxylic acids (2) and 3-phenylcarbostyrils (8).Under similar conditions 3-chloro-α-phenylcinnamic acids (5) furnish 3-phenylcoumarins (6).
- Kessar, S. V.,Nadir, U. K.,Gupta, Y. P.,Pahwa, P. S.,Singh, Paramjit
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