605-48-1Relevant articles and documents
Biocatalytic chlorination of aromatic hydrocarbons by chloroperoxidase of caldariomyces fumago
Vazquez-Duhalt, Rafael,Ayala, Marcela,Marquez-Rocha, Facundo J.
, p. 929 - 933 (2001)
Chloroperoxidase from Caldariomyces fumago was able to chlorinate 17 of 20 aromatic hydrocarbons assayed in the presence of hydrogen peroxide and chloride ions. Reaction rates varied from 0.6 min-1 for naphthalene to 758 min-1 for 9-methylanthracene. Mono-, di- and tri-chlorinated compounds were obtained from the chloroperoxidase-mediated reaction on aromatic compounds. Dichloroacenaphthene, trichloroacenaphthene 9,10-dichloroanthracene, chloropyrene, dichloropyrene, dichlorobiphenylene and trichlorobiphenylene were identified by mass spectral analyses as products from acenaphthene, anthracene, pyrene and biophenylene respectively. Polycyclic aromatic hydrocarbons with 5 and 6 aromatic rings were also substrates for the chloroperoxidase reaction. The importance of the microbial chlorination of aromatic pollutants and its potential environmental impact are discussed.
Akiyama et al.
, p. 3443 (1971)
A practical lewis base catalyzed electrophilic chlorination of arenes and heterocycles
Maddox, Sean M.,Nalbandian, Christopher J.,Smith, Davis E.,Gustafson, Jeffrey L.
supporting information, p. 1042 - 1045 (2015/03/30)
A mild phosphine sulfide catalyzed electrophilic halogenation of arenes and heterocycles that utilizes inexpensive and readily available N-halosuccinimides is disclosed. This methodology is shown to efficiently chlorinate diverse aromatics, including simple arenes such as anthracene, and heterocycles such as indoles, pyrrolopyrimidines, and imidazoles. Arenes with Lewis acidic moieties also proved amenable, underscoring the mild nature of this chemistry. Lewis base catalysis was also found to improve several diverse aromatic brominations and iodinations.
Features of the Diels-Alder reaction between 9,10-diphenylanthracene and 4-phenyl-1,2,4-triazoline-3,5-dione
Kiselev,Kornilov,Kashaeva,Potapova,Krivolapov,Litvinov,Konovalov
, p. 2073 - 2080 (2015/02/19)
The Diels-Alder reaction between substituted anthracenes 1a-1j and 4-phenyl-1,2,4-triazoline-3,5 (2) is studied. In all cases except one, the reaction proceeds on the most active 9,10-atoms of substituted anthracenes. The orthogonality of the two phenyl groups at the 9,10-position of diene 1a is found to shield 9,10-reactive centers. No dienophiles with C=C bonds are shown to participate in the Diels-Alder reaction with 1a; however, the reaction 1a + 2 proceeds with the very active dienophile 2,4-phenyl-1,2,4-triazoline-3,5-dione. It is shown that attachment occurs on the less active but sterically accessible 1,4-reactive center of diene 1a. The structure of adduct 3a is proved by 1H and 13C NMR spectroscopy and X-ray diffraction analysis. The following parameters are obtained for reaction 1a + 2 ? 3a in toluene at 25°C: Keq = 2120 M-1, ΔHf≠ = 58.6 kJ/mol, ΔSf≠ = -97 J/(mol K), ΔVf≠ = -17.2 cm3/mol, ΔHb ≠ = 108.8 kJ/mol, ΔSb≠ = 7.3 J/(mol K), ΔVb≠ = -0.8 cm3/mol, ΔHr-n = -50.2 kJ/mol, ΔSr-n = -104.3 J/(mol K), ΔVr-n = -15.6 cm3/mol. It is concluded that the values of equilibrium constants of the reactions 1a-1j + 2 ? 3a-3j vary within 4 × 101-1011 M-1.
