Dediazoniation reactions of arenediazonium ions under solvolytic conditions:: fluoride anion abstraction from trifluoroethanol and α-hydrogen atom abstraction from ethanol

被引:25
作者
Canning, PSJ [1 ]
McCrudden, K [1 ]
Maskill, H [1 ]
Sexton, B [1 ]
机构
[1] Univ Newcastle Upon Tyne, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England
关键词
D O I
10.1039/a804686g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Arenediazonium salts decompose thermally and photochemically in trifluoroethanol to yield trifluoroethyl ethers and (in part by fluoride abstraction from the solvent) fluoroarenes; the less reactive compounds in trifluoroethanol decompose readily in ethanol to give arenes in a radical reaction involving abstraction of the ct-hydrogen from the ethanol.
引用
收藏
页码:1971 / 1972
页数:2
相关论文
共 17 条
[1]   On aromatic fluoric compounds, I A new method for its representation [J].
Balz, G ;
Schiemann, G .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1927, 60 :1186-1190
[2]   SECONDARY DEUTERIUM KINETIC ISOTOPE EFFECTS IN THE SOLVOLYSIS OF 4-TERT-BUTYLCYCLOHEXYL AND BICYCLO[3.2.1]OCTAN-3-YL TOLUENE-PARA-SULFONATES - NEW RESULTS USING 50-PERCENT-AQUEOUS ETHANOL, ACETIC-ACID, AND 97-PERCENT-AQUEOUS HEXAFLUOROPROPAN-2-OL [J].
BANKS, RM ;
MASKILL, H ;
NATARAJAN, R ;
WILSON, AA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (02) :427-431
[3]  
BERGSTROM RG, 1974, TETRAHEDRON LETT, P2975
[4]   DEDIAZONIATION OF ARENEDIAZONIUM IONS IN HOMOGENEOUS SOLUTION .7. INTERMEDIACY OF PHENYL CATION [J].
BERGSTROM, RG ;
LANDELLS, RGM ;
WAHL, GH ;
ZOLLINGER, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (11) :3301-3305
[5]   THERMOLYSIS OF ARENEDIAZONIUM IONS IN ACIDIC METHANOL - EVIDENCE FOR COMPETING, INDEPENDENT IONIC AND RADICAL MECHANISMS [J].
BUNNETT, JF ;
YIJIMA, C .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) :639-642
[6]   Chemical constitution and reactivity I Phenyldiazonium chloride and its mono substituted derivatives [J].
Crossley, ML ;
Kienle, RH ;
Benbrook, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :1400-1404
[7]   THE MECHANISMS OF DIAZONIUM SALT REACTIONS .2. A REDETERMINATION OF THE RATES OF THE THERMAL DECOMPOSITION OF 6-DIAZONIUM SALTS IN AQUEOUS SOLUTION [J].
DETAR, DF ;
BALLENTINE, AR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1956, 78 (16) :3916-3920
[8]   MECHANISMS OF DIAZONIUM SALT REACTIONS .6. THE REACTIONS OF DIAZONIUM SALTS WITH ALCOHOLS UNDER ACIDIC CONDITIONS - EVIDENCE FOR HYDRIDE TRANSFER [J].
DETAR, DF ;
KOSUGE, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1958, 80 (22) :6072-6077
[9]   RATE AND PRODUCT ANALYTICAL STUDY OF THE SOLVOLYSIS OF 3-CHLOROBENZYL ARENESULFONATES IN AQUEOUS 2,2,2-TRIFLUOROETHANOL [J].
GORDON, IM ;
MASKILL, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1991, (12) :1951-1953
[10]   DEDIAZONIATION OF ARENEDIAZONIUM IONS IN HOMOGENEOUS SOLUTION .11. EVIDENCE FOR 2 INTERMEDIATES IN REACTION OF 2,4,6-TRIMETHYLBENZENEDIAZONIUM ION IN 2,2,2-TRIFLUOROETHANOL [J].
HASHIDA, Y ;
LANDELLS, RGM ;
LEWIS, GE ;
SZELE, I ;
ZOLLINGER, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (09) :2816-2823