1625-84-9Relevant articles and documents
Synthesis of ferrocenyl derivatives of anthracene
Roberts, R.M.G.
, p. 181 - 186 (1990)
1-Ferrocenylanthraquinone has been synthesised from the cheap and commercially available 1-diazoniumanthraquinone (Aldrich Fast Red Al salt).Reduction of this anthraquinone with aluminium alkoxide has given good yields of 1-ferrocenyl-anthracene, the first preparation of such polycyclic ferrocenes.The TCNE adduct of the anthracene was prepared in good yield, in marked contrast to the outcome of the redox reaction of ferrocene itself with TCNE.No oxidation was observed with TCNQ.Diels-Alder addition of benzyne resulted in a very low yield (ca. 1 percent)of 1-ferrocentyltriptycene.The 1H and 13C NMR spectra are reported, and discussed in detail together with 57Fe Moessbauer data.
Diels-Alder reaction rate in the solid state and the evidence of the location of molecular complexes between the reagents on the reaction pathway
Kiselev, Vladimir D.,Kolesnikova, Anastasia O.,Dinikaev, Ildar F.,Shulyatiev, Alexey A.,Klimovitskii, Alexander E.,Kornilov, Dmitry A.
, p. 207 - 212 (2020/10/02)
The rate of reactions in the solid phase with uniform grinding of crystals of dienes, anthracene, and 9,10-dimethylanthracene, with dienophiles, tetracyanoethylene, N-phenylmaleimide, and 4-phenyl-1,2,4-triazoline-3,5-dione, has been studied. It was shown
Theoretical and structural analysis of long C-C bonds in the adducts of polycyanoethylene and anthracene derivatives and their connection to the reversibility of diels-alder reactions
Hirsch, Anna K. H.,Reutenauer, Philippe,Le Moignan, Marc,Ulrich, Sebastien,Boul, Peter J.,Harrowfield, Jack M.,Jarowski, Peter D.,Lehn, Jean-Marie
, p. 1073 - 1080 (2014/02/14)
X-ray structure determinations on four Diels-Alder adducts derived from the reactions of cyano- and ester-substituted alkenes with anthracene and 9,10-dimethylanthracene have shown the bonds formed in the adduction to be particularly long. Their lengths range from 1.58 to 1.62 A, some of the longest known for Diels-Alder adducts. Formation of the four adducts is detectably reversible at ambient temperature and is associated with free energies of reaction ranging from -2.5 to -40.6 kJ mol-1. The solution equilibria have been experimentally characterised by NMR spectroscopy. Density-functional-theory calculations at the MPW1K/6-31+G(d,p) level with PCM solvation agree with experiment with average errors of 6 kJ mol-1 in free energies of reaction and structural agreement in adduct bond lengths of 0.013 A. To understand more fully the cause of the reversibility and its relationship to the long adduct bond lengths, natural-bond-orbital (NBO) analysis was applied to quantify donor-acceptor interactions within the molecules. Both electron donation into the σ-anti-bonding orbital of the adduct bond and electron withdrawal from the σ-bonding orbital are found to be responsible for this bond elongation. Copyright
Charge-transfer complex formation and photo-induced electron-transfer reaction of dibenzo-7-silabicyclo[2.2.1]hepta-2,5-dienes
Kako, Masahiro,Mori, Masahiro,Hatakenaka, Kaname,Kakuma, Seiji,Nakadaira, Yasuhiro,Yasui, Masanori,Iwasaki, Fujiko
, p. 1265 - 1274 (2007/10/03)
Dibenzo-7-silabicyclo[2.2.1]hepta-2,5-dienes (1a, 1b) are excellent electron donors because of effective σ-π conjugation between the orbitals of C-C π bonds and Si-C σ bonds. Some of their donor properties are demonstrated by the reactions with some electron accepters. When 1a and 1b are mixed with tetracyanoethylene, facile formation of charge-transfer complexes was observed. In the 2,4,6-triphenylpyrylium tetrafluoroborate-sensitized photoreaction of 1b, the corresponding difluorosilane and anthracene were obtained in good yields. The structural and electronic features of radical cation 1a+. were provided by semiempericaI molecular orbital calculation. In addition, the structure of 1a in crystals was determined by X-ray crystallography and compared with that obtained by the calculation.
