ROLE COPPER CHLORIDES IN SANDMEYER AND MEERWEIN REACTIONS

被引:31
作者
DICKERMAN, SC
DESOUZA, DJ
JACOBSON, N
机构
[1] Department of Chemistry, New York University, University Heights
关键词
D O I
10.1021/jo01255a048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The mechanism of the Meerwein reaction of p-chlorobenzendiazonium chloride with several monomers has been studied by determining the variation in the composition of the products of these reactions with initial concentration of cupric chloride. The results are inexplicable in terms of mechanisms for the Meerwein reaction that involve complexes of monomer with either cuprous or cupric chloride but are consistent with a three-way competition for a common intermediate, the p-chlorophenyl radical. Relative reactivities for the addition of this radical to the several monomers have also been measured. © 1969, American Chemical Society. All rights reserved.
引用
收藏
页码:710 / +
页数:1
相关论文
共 30 条
[1]   DIRECTIVE EFFECTS IN ATTACK OF PHENYL RADICALS ON CARBON-HYDROGEN BONDS [J].
BRIDGER, RF ;
RUSSELL, GA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (23) :3754-&
[2]   *EINWIRKUNG AROMATISCHER DIAZONIUMSALZE AUF UNGESATTIGTE VERBINDUNGEN [J].
BRUNNER, WH ;
KUSTATSCHER, J .
MONATSHEFTE FUR CHEMIE, 1951, 82 (01) :100-106
[3]   *UBER DIE UMSETZUNG VON ACRYLSAURENITRIL MIT AROMATISCHEN DIAZONIUMSALZEN [J].
BRUNNER, WH ;
PERGER, H .
MONATSHEFTE FUR CHEMIE, 1948, 79 (3-4) :187-197
[4]  
Cowdrey W.A., 1949, J CHEM SOC, V48, pS48, DOI [10.1039/JR9490000S48, DOI 10.1039/JR9490000S48]
[5]   THE KINETICS OF THE SANDMEYER AND MEERWEIN REACTIONS [J].
DICKERMAN, SC ;
WEISS, K ;
INGBERMAN, AK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (08) :1904-1911
[6]   HOMOLYTIC PHENYLATION OF BENZENE, NAPHTHALENE AND ANTHRACENE IN PRESENCE OF COPPER SALTS - CORRELATION OF PARTIAL RATE FACTORS WITH LOCALIZATION ENERGIES [J].
DICKERMAN, SC ;
VERMONT, GB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (21) :4150-&
[7]   RELATIVE REACTIVITIES AND LINEAR FREE-ENERGY RELATIONSHIPS IN COMPETITIVE ADDITION OF SUBSTITUTED PHENYL RADICALS TO VINYL MONOMERS [J].
DICKERMAN, SC ;
DESOUZA, DJ ;
FRYD, M ;
MEGNA, IS ;
SKOULTCH.MM .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (03) :714-+
[8]   CUPROUS CHLORIDE CATALYZED 2,4-DICHLORO-PHENYLATION OF BENZENE IN AQUEOUS ACETONE - THE MECHANISM OF THE MEERWEIN REACTION [J].
DICKERMAN, SC ;
WEISS, K ;
INGBERMAN, AK .
JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (03) :380-381
[9]   HOMOLYTIC AROMATIC SUBSTITUTION .V. PHENYLATION OF PHENANTHRENE [J].
DICKERMAN, SC ;
ZIMMERMAN, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (22) :5048-&
[10]   RELATIVE ARYL RADICAL AFFINITIES OF MONOMERS [J].
DICKERMAN, SC ;
MEGNA, IS ;
SKOULTCHI, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (09) :2270-2271