PROTONATION AND ACID-CATALYZED HYDROLYSIS OF NITROSOARYL ETHERS

被引:5
作者
MOODIE, RB
OSULLIVAN, B
机构
[1] University of Exeter, Exeter
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 1995年 / 02期
关键词
D O I
10.1039/p29950000205
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Studies of the equilibrium protonation and kinetics of acid catalysed hydrolysis of 4-nitrosoanisole, 4-nitrosophenyl phenyl ether and related compounds in dilute aqueous acid and in concentrated aqueous trifluoroacetic acid are reported. Hydrolysis is remarkably facile and occurs by nucleophilic attack of water at the ring carbon bearing the alkoxy or aryloxy substituent of the protonated nitroso aromatic. Direct and indirect pK(a) determinations for nitroso protonation are reported.
引用
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页码:205 / 208
页数:4
相关论文
共 19 条
[1]  
ALOBAIDI U, 1986, THESIS EXETER
[2]  
BELYAEV EY, 1974, ZH OBSHCH KHIM+, V44, P856
[3]   MECHANISM OF ACID-CATALYZED HYDROLYSIS OF AZOARYL ETHERS [J].
BUNNETT, JF ;
BUNCEL, E ;
NAHABEDIAN, KV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (21) :4136-&
[4]   CHEMISTRY OF NITROSO-COMPOUNDS .2. NITROSATION OF PHENOL AND ANISOLE [J].
CHALLIS, BC ;
LAWSON, AJ .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (04) :770-&
[5]   CHEMISTRY OF NITROSO-COMPOUNDS .3. NITROSATION OF SUBSTITUTED BENZENES IN CONCENTRATED ACIDS [J].
CHALLIS, BC ;
LAWSON, AJ ;
HIGGINS, RJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (12) :1831-&
[6]   MECHANISMS OF CLEAVAGE OF HETEROAROMATIC ETHERS .2. ACID-CATALYZED CLEAVAGE OF 2-METHOXYPYRIMIDINE-O18 [J].
DANIELS, R ;
GRADY, LT ;
BAUER, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (07) :1531-&
[7]   NITROSATION AND NITROUS ACID-CATALYZED NITRATION OF ANISOLE AND 2,6-DIMETHYLANISOLE [J].
DIX, LR ;
MOODIE, RB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1986, (07) :1097-1101
[8]   AROMATIC REACTIVITY .32. DETRITIATION AND DESILYLATION IN TRIFLUOROACETIC ACID . SOLVENT ISOTOPE EFFECT AND INFLUENCE OF ADDED WATER AND SALTS [J].
EABORN, C ;
JACKSON, PM ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1966, (07) :613-&
[9]   IONIZATION OF CARBONYL-COMPOUNDS IN SULFURIC-ACID - CORRECTION FOR MEDIUM EFFECTS BY CHARACTERISTIC VECTOR ANALYSIS [J].
EDWARD, JT ;
WONG, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (13) :4229-4232
[10]   SELECTIVE RAPID TRANSFER-HYDROGENATION OF AROMATIC NITRO-COMPOUNDS [J].
ENTWISTLE, ID ;
JOHNSTONE, RAW ;
POVALL, TJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (13) :1300-1301