2,2'-4,4''-4',4'''-QUATERPYRIDYL - A BUILDING BLOCK FOR THE PREPARATION OF NOVEL REDOX REAGENTS .1. PREPARATION AND QUATERNIZATION

被引:36
作者
MORGAN, RJ [1 ]
BAKER, AD [1 ]
机构
[1] CUNY QUEENS COLL,DEPT CHEM,FLUSHING,NY 11367
关键词
D O I
10.1021/jo00294a007
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient preparation of 2,2':4,':4',4'Flushing, New York 11367-quaterpyridyl (qpy) from 4,4'-bipyridine is described, using palladium on charcoal. Conditions are described for the selective methylation of the nitrogen atoms present. This has allowed the preparation of mono- and dimethylquaternary salts that retain an a-diimine site for complexation to a metal. These quaternary salts can be used to prepare complexes in which metal ions are coordinated to viologen-type ligands. Electrochemical and spectroscopic measurements of the diquaternary salt derived from qpy suggest that it behaves as two separate or weakly interacting monoquat moieties. © 1990, American Chemical Society. All rights reserved.
引用
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页码:1986 / 1993
页数:8
相关论文
共 44 条
[1]   PHOTOINDUCED HYDROGEN EVOLUTION WITH A VIOLOGEN-LINKED PORPHYRIN [J].
AONO, S ;
KAJI, N ;
OKURA, I .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (02) :170-171
[2]   STABLE POTASSIUM COMPLEX OF A PYRIDINE-FUSED HEXAAZA[18]ANNULENE - A NEW RIVAL FOR 18-CROWN-6 [J].
BELL, TW ;
GUZZO, F .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (20) :6111-6112
[3]   SPECTROSCOPIC AND ELECTROCHEMICAL PROPERTIES OF THE DIMER TETRAKIS(2,2'-BIPYRIDINE)(MU-2,3-BIS(2-PYRIDYL)PYRAZINE)DIRUTHENIUM(II) AND ITS MONOMERIC ANALOG [J].
BRAUNSTEIN, CH ;
BAKER, AD ;
STREKAS, TC ;
GAFNEY, HD .
INORGANIC CHEMISTRY, 1984, 23 (07) :857-864
[4]  
Bruinink J, 1977, J ELECTROCHEM SOC, V124, P1854, DOI 10.1149/1.2133534
[5]   Researches on the polypyridyls. [J].
Burstall, FH .
JOURNAL OF THE CHEMICAL SOCIETY, 1938, :1662-1672
[6]   NUCLEAR MAGNETIC RESONANCE SPECTRA OF 2,2'-BIPYRIDYL [J].
CASTELLANO, S ;
GUNTHER, H ;
EBERSOLE, S .
JOURNAL OF PHYSICAL CHEMISTRY, 1965, 69 (12) :4166-+
[7]   DIQUATERNARY SALTS .1. PREPARATION AND CHARACTERIZATION OF DIQUATERNARY SALTS OF SOME DIAZINES AND DIAZOLES [J].
CURPHEY, TJ ;
PRASAD, KS .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (14) :2259-&
[8]   SPECIFIC AND SELECTIVE REDUCTION OF AROMATIC NITROGEN-HETEROCYCLES WITH THE BIS-PYRIDINE COMPLEXES OF BIS(1,4-DIHYDRO-1-PYRIDYL)ZINC AND "BIS(1,4-DIHYDRO-1-PYRIDYL)MAGNESIUM [J].
DEKONING, AJ ;
BUDZELAAR, PHM ;
BOERSMA, J ;
VANDERKERK, GJM .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 199 (02) :153-169
[9]  
DERONZIER A, 1982, NOUV J CHIM, V6, P97
[10]   PICOSECOND PHOTOCHEMISTRY OF METHYL VIOLOGEN [J].
EBBESEN, TW ;
MANRING, LE ;
PETERS, KS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (24) :7400-7404