메뉴 건너뛰기




Volumn 77, Issue 9, 2009, Pages 1242-1248

Monofluorinated analogues of polychlorinated biphenyls (F-PCBs): Synthesis using the Suzuki-coupling, characterization, specific properties and intended use

Author keywords

Aromatic boronic acids; Internal standards; Markers; Mass spectrometry; Monofluorinated polychlorinated biphenyls (F PCBs); NMR; Physico chemical properties; Polychlorinated biphenyls (PCBs); Suzuki coupling; Tracers

Indexed keywords

CHEMICAL BONDS; CHEMICAL REACTIONS; FLUORINE; ISOMERS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PHYSICOCHEMICAL PROPERTIES; POLYCHLORINATED BIPHENYLS; RADIOACTIVE TRACERS;

EID: 71749117732     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2006.02.029     Document Type: Article
Times cited : (24)

References (23)
  • 1
    • 0032949055 scopus 로고    scopus 로고
    • Electonspray ionization mass spectrometry detection of intermediates in the palladium-catalyzed oxidative self-coupling of areneboronic acids
    • Aramendia M.A., and Lafont F. Electonspray ionization mass spectrometry detection of intermediates in the palladium-catalyzed oxidative self-coupling of areneboronic acids. J. Org. Chem. 64 (1999) 3592-3594
    • (1999) J. Org. Chem. , vol.64 , pp. 3592-3594
    • Aramendia, M.A.1    Lafont, F.2
  • 2
    • 34250257755 scopus 로고
    • Analysis of polychlorinated biphenyls (PCB) by glass capillary gas chromatography
    • Ballschmiter K., and Zell M. Analysis of polychlorinated biphenyls (PCB) by glass capillary gas chromatography. Fresenius Z. Anal. Chem. 302 (1980) 20-31
    • (1980) Fresenius Z. Anal. Chem. , vol.302 , pp. 20-31
    • Ballschmiter, K.1    Zell, M.2
  • 4
    • 0037752720 scopus 로고    scopus 로고
    • Introduction: PCB properties, uses, occurrence, and regulator history
    • Robertson L.W., and Hansen L.G. (Eds), The University Press of Kentrucky, USA
    • Erickson M.D. Introduction: PCB properties, uses, occurrence, and regulator history. In: Robertson L.W., and Hansen L.G. (Eds). PCBs Recent Advantages in Environmental Toxicology and Health Effects (2001), The University Press of Kentrucky, USA
    • (2001) PCBs Recent Advantages in Environmental Toxicology and Health Effects
    • Erickson, M.D.1
  • 5
    • 85065137145 scopus 로고
    • The Ullmann synthesis of biaryls
    • Fanta P.E. The Ullmann synthesis of biaryls. Synthesis (1974) 9-21
    • (1974) Synthesis , pp. 9-21
    • Fanta, P.E.1
  • 6
    • 0027424568 scopus 로고
    • Concise synthesis of belamcandaquinones A and B by palladium(0) catalyzed cross-coupling reaction of bromoquinone with arylboronic acids
    • Fukuyama Y., Kiriyama Y., and Kodama M. Concise synthesis of belamcandaquinones A and B by palladium(0) catalyzed cross-coupling reaction of bromoquinone with arylboronic acids. Tetrahedron Lett. 34 (1993) 7637-7638
    • (1993) Tetrahedron Lett. , vol.34 , pp. 7637-7638
    • Fukuyama, Y.1    Kiriyama, Y.2    Kodama, M.3
  • 8
    • 33947438555 scopus 로고
    • Electronic effects of fluorine
    • Jones R.N. Electronic effects of fluorine. J. Am. Chem. Soc. 67 (1945) 2127-2132
    • (1945) J. Am. Chem. Soc. , vol.67 , pp. 2127-2132
    • Jones, R.N.1
  • 9
    • 0001322607 scopus 로고
    • Facile aryl-aryl exchange between the palladium center and phosphine ligands in the palladium(II) complexes
    • Kong K.C., and Cheng C.H. Facile aryl-aryl exchange between the palladium center and phosphine ligands in the palladium(II) complexes. J. Am. Chem. Soc. 113 (1991) 6313-6315
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6313-6315
    • Kong, K.C.1    Cheng, C.H.2
  • 10
    • 0034855977 scopus 로고    scopus 로고
    • Synthesis of polychlorinated biphenyls (PCBs) using the Suzuki-coupling
    • Lehmler H.J., and Robertson S.W. Synthesis of polychlorinated biphenyls (PCBs) using the Suzuki-coupling. Chemosphere 45 (2001) 137-143
    • (2001) Chemosphere , vol.45 , pp. 137-143
    • Lehmler, H.J.1    Robertson, S.W.2
  • 11
    • 0003255052 scopus 로고    scopus 로고
    • Monofluorinated polycyclic aromatic hydrocarbons: standards in environmental chemistry and biochemical applications
    • Neilson A.H. (Ed), Springer Verlag, Berlin, Germany
    • Luthe G., Ariese F., and Brinkman U.A.Th. Monofluorinated polycyclic aromatic hydrocarbons: standards in environmental chemistry and biochemical applications. In: Neilson A.H. (Ed). Handbook of Environmental Chemistry: Organic Fluorine Compounds (2002), Springer Verlag, Berlin, Germany
    • (2002) Handbook of Environmental Chemistry: Organic Fluorine Compounds
    • Luthe, G.1    Ariese, F.2    Brinkman, U.A.Th.3
  • 12
    • 0036972045 scopus 로고    scopus 로고
    • Suzuki cross-coupling reactions of aryl halides in phosphonium salt ionic liquid under mild conditions
    • McNulty J., Capretta A., Wilson J., Dyck J., Adjabeng G., and Robertson A. Suzuki cross-coupling reactions of aryl halides in phosphonium salt ionic liquid under mild conditions. Chem. Commun. (2002) 1986-1991
    • (2002) Chem. Commun. , pp. 1986-1991
    • McNulty, J.1    Capretta, A.2    Wilson, J.3    Dyck, J.4    Adjabeng, G.5    Robertson, A.6
  • 13
    • 2042507954 scopus 로고
    • Palladium-catalyzed cross-coupling reactions of organoboron compounds
    • Miyaura N., and Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chem. Rev. 95 (1995) 2457-2483
    • (1995) Chem. Rev. , vol.95 , pp. 2457-2483
    • Miyaura, N.1    Suzuki, A.2
  • 14
    • 0742313889 scopus 로고    scopus 로고
    • Palladium catalyzed Suzuki-type self-coupling of arylboronic acids: a mechanism study
    • Moreno-Manas M., Perez M., and Pleixats R. Palladium catalyzed Suzuki-type self-coupling of arylboronic acids: a mechanism study. J. Org. Chem. 61 (1996) 2346-2351
    • (1996) J. Org. Chem. , vol.61 , pp. 2346-2351
    • Moreno-Manas, M.1    Perez, M.2    Pleixats, R.3
  • 15
    • 0015892514 scopus 로고
    • Polychlorinated biphenyls. VI. 2,3,7,8-Tetrachlorodibenzofuran, a critical byproduct in the synthesis of 2,2′,4,4′,5,5′-hexachloro-biphenyl by the Ullmann reaction
    • Moron M., Sundström G., and Wachtmeister C.A. Polychlorinated biphenyls. VI. 2,3,7,8-Tetrachlorodibenzofuran, a critical byproduct in the synthesis of 2,2′,4,4′,5,5′-hexachloro-biphenyl by the Ullmann reaction. Acta Chem. Scand. 27 (1973) 3121-3122
    • (1973) Acta Chem. Scand. , vol.27 , pp. 3121-3122
    • Moron, M.1    Sundström, G.2    Wachtmeister, C.A.3
  • 16
    • 0025735743 scopus 로고
    • A new strategy for he synthesis of biflavonoids via arylboronic acids
    • Müller D., and Fleury J.P. A new strategy for he synthesis of biflavonoids via arylboronic acids. Tetrahedron Lett. 32 (1991) 2229-2232
    • (1991) Tetrahedron Lett. , vol.32 , pp. 2229-2232
    • Müller, D.1    Fleury, J.P.2
  • 17
    • 0001856758 scopus 로고
    • Gram quantity synthesis and chromatographic assessment of 3,3′4,4′-tetrachlorobiphenyl
    • Nakatsu K., Brien J.F., Taub H., Racz W.J., and Marks G.S. Gram quantity synthesis and chromatographic assessment of 3,3′4,4′-tetrachlorobiphenyl. J. Chromatogr. 239 (1982) 97-103
    • (1982) J. Chromatogr. , vol.239 , pp. 97-103
    • Nakatsu, K.1    Brien, J.F.2    Taub, H.3    Racz, W.J.4    Marks, G.S.5
  • 18
    • 0026786545 scopus 로고
    • Palladium catalyzed coupling of halobenzenes with arylboronic acids: role of the triphenlyphosphine ligand
    • O'Keefe D.F., Dannock M.C., and Marcuccio S.M. Palladium catalyzed coupling of halobenzenes with arylboronic acids: role of the triphenlyphosphine ligand. Tetrahedron Lett. 33 (1992) 882-6680
    • (1992) Tetrahedron Lett. , vol.33 , pp. 882-6680
    • O'Keefe, D.F.1    Dannock, M.C.2    Marcuccio, S.M.3
  • 19
    • 33751155220 scopus 로고
    • Equilibration of the oxidative addition product of tetrakis(triphenylphosphine)palladium and electron rich aryl halides leads to product scrambling in the Stille reaction
    • Segelstein B.E., Bulter T.W., and Chenard B.L. Equilibration of the oxidative addition product of tetrakis(triphenylphosphine)palladium and electron rich aryl halides leads to product scrambling in the Stille reaction. J. Org. Chem. 60 (1995) 12-13
    • (1995) J. Org. Chem. , vol.60 , pp. 12-13
    • Segelstein, B.E.1    Bulter, T.W.2    Chenard, B.L.3
  • 20
    • 0000564666 scopus 로고    scopus 로고
    • High yields of symmetrical biaryls from palladium catalysed homocoupling of arylboronic acids under mild conditions
    • Smith K.A., Campi E.M., Jackson W.R., Maruccio S., Naeslund C.G.M., and Deacon G.B. High yields of symmetrical biaryls from palladium catalysed homocoupling of arylboronic acids under mild conditions. Synlett (1997) 131-132
    • (1997) Synlett , pp. 131-132
    • Smith, K.A.1    Campi, E.M.2    Jackson, W.R.3    Maruccio, S.4    Naeslund, C.G.M.5    Deacon, G.B.6
  • 21
    • 0032518829 scopus 로고    scopus 로고
    • Catalytic cross-coupling reactions in biaryl synthesis
    • Stanforth S.P. Catalytic cross-coupling reactions in biaryl synthesis. Tetrahedron 54 (1998) 263-303
    • (1998) Tetrahedron , vol.54 , pp. 263-303
    • Stanforth, S.P.1
  • 22
    • 0346786657 scopus 로고    scopus 로고
    • Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles
    • Suzuki A. Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles. J. Organomet. Chem. 576 (1999) 147-168
    • (1999) J. Organomet. Chem. , vol.576 , pp. 147-168
    • Suzuki, A.1
  • 23
    • 0028641179 scopus 로고
    • The Dutch PCB/dioxin study development of a method for the determination of dioxins, planar and other PCBs in human milk
    • Tuinstra L.G.M., Traag W.A., van Rhijn J.A., and Spreng P.F. The Dutch PCB/dioxin study development of a method for the determination of dioxins, planar and other PCBs in human milk. Chemosphere 29 (1994) 1859-1875
    • (1994) Chemosphere , vol.29 , pp. 1859-1875
    • Tuinstra, L.G.M.1    Traag, W.A.2    van Rhijn, J.A.3    Spreng, P.F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.