INTRAMOLECULAR-CATALYZED SULFONAMIDE HYDROLYSIS .8. INTRAMOLECULAR NUCLEOPHILIC CATALYSIS BY THE NEIGHBORING HYDROXYL GROUP IN ACID-CATALYZED BENZENESULFONAMIDE HYDROLYSIS

被引：9

作者：

WAGENAAR, A

KIRBY, AJ

ENGBERTS, JBFN

机构：

[1] STATE UNIV GRONINGEN,DEPT ORGAN CHEM,9747 AG GRONINGEN,NETHERLANDS

[2] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1984年 / 49卷 / 19期

关键词：

D O I：

10.1021/jo00193a001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

引用

页码：3445 / 3448

页数：4

共 24 条

[1] CONVENIENT METHOD FOR SULFONAMIDE CLEAVAGE [J].

CARPENTE.PD ;

LENNON, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (18) :664-665

[2] FORMATION AND HYDROLYSIS OF LACTONES OF PHENOLIC-ACIDS [J].

CASWELL, M ;

SCHMIR, GL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (14) :4815-4821

[3] STERIC ACCELERATION OF LACTONIZATION REACTIONS - ANALYSIS OF STEREOPOPULATION-CONTROL [J].

DANFORTH, C ;

NICHOLSON, AW ;

JAMES, JC ;

LOUDON, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (14) :4275-4281

[4] QUANTITATIVE-EVALUATION OF STERIC EFFECTS IN SN2 RING-CLOSURE REACTIONS [J].

DETAR, DF ;

LUTHRA, NP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (13) :4505-4512

[5] INTRAMOLECULAR CARBOXYL-CATALYZED HYDROLYSIS OF SULFONAMIDE .4. SALT EFFECTS ON THE INTRAMOLECULAR CARBOXYL-CATALYZED HYDROLYSIS OF SULFONAMIDES [J].

GRAAFLAND, T ;

KIRBY, AJ ;

ENGBERTS, JBF .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (01) :215-217

[6] STERIC EFFECTS IN THE INTRAMOLECULAR CARBOXYL-CATALYZED HYDROLYSIS OF SULFONAMIDES - ABINITIO QUANTUM CHEMICAL STUDIES OF THE PENTA-COORDINATED SULFUR INTERMEDIATE [J].

GRAAFLAND, T ;

NIEUWPOORT, WC ;

ENGBERTS, JBFN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (15) :4490-4494

[7] STRUCTURE AND REACTIVITY IN INTRA-MOLECULAR CATALYSIS .4. CATALYSIS OF SULFONAMIDE HYDROLYSIS BY THE NEIGHBORING CARBOXYL GROUP [J].

GRAAFLAND, T ;

WAGENAAR, A ;

KIRBY, AJ ;

ENGBERTS, JBFN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (23) :6981-6990

[8] INTRAMOLECULAR CATALYSIS OF SULFONAMIDE HYDROLYSIS .3. INTRAMOLECULAR ACID-CATALYZED HYDROLYSIS OF (Z)-2-CARBOXY-N-METHYL-N-PHENYLETHENESULFONAMIDE AND N-METHYL-N-PHENYLMALEAMIC ACID UNDER CONDITIONS OF VARYING WATER ORDERING EFFECTS [J].

GRAAFLAND, T ;

ENGBERTS, JBFN ;

KIRBY, AJ .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (14) :2462-2465

[9] INTRAMOLECULAR-CATALYZED SULFONAMIDE HYDROLYSIS .7. THE THORPE-INGOLD EFFECT IN THE INTRAMOLECULAR CARBOXYL-CATALYZED HYDROLYSIS OF SULFONAMIDES [J].

JAGER, J ;

GRAAFLAND, T ;

SCHENK, H ;

KIRBY, AJ ;

ENGBERTS, JBFN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (01) :139-143

[10] ENZYMATIC AND NONENZYMATIC REACTIONS OF CYCLIC SULFONATE AND SULFATE ESTERS [J].

KAISER, ET .

ACCOUNTS OF CHEMICAL RESEARCH, 1970, 3 (05) :145-&

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