INTRAMOLECULAR-CATALYZED HYDROLYSIS OF SULFONAMIDES .10. INTRAMOLECULAR NUCLEOPHILIC CATALYSIS BY THE NEIGHBORING HYDROXYL GROUP IN ACID-CATALYZED AND BASE-CATALYZED-HYDROLYSIS OF AROMATIC SULFONAMIDES AND SULTONES - MECHANISM OF INTRAMOLECULAR NUCLEOPHILIC-SUBSTITUTION AT SULFONYL SULFUR

被引：10

作者：

WAGENAAR, A ^{[1
]}

ENGBERTS, JBFN ^{[1
]}

机构：

[1] STATE UNIV GRONINGEN,DEPT ORGAN CHEM,NIJENBORGH 16,9747 AG GRONINGEN,NETHERLANDS

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1988年 / 53卷 / 04期

关键词：

D O I：

10.1021/jo00239a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

引用

页码：768 / 772

页数：5

共 32 条

[1]

ALDER RW, 1971, MECHANISM ORGANIC CH, P204

[2] The formation and stabillity of spiro-compounds. Part I. Spiro-compounds from cyclo-hexane. [J].

Beesley, RM ;

Ingold, CK ;

Thorpe, JF .

JOURNAL OF THE CHEMICAL SOCIETY, 1915, 107 :1080-1106

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

CASWELL, M ;

SCHMIR, GL .

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

[4] NATURE OF ELECTRICAL EFFECT OF ALKYL-GROUPS .1. VALIDITY OF SIGMA-STAR CONSTANTS [J].

CHARTON, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (17) :5687-5688

[5]

CHARTON M, 1976, J ORG CHEM, V41, P903

[6]

Charton M., 1981, Prog. Phys. Org. Chem, P119, DOI 10.1002/9780470171929.ch3

[7] ON THE ORIGIN OF PROXIMITY EFFECTS ON REACTIVITY - A MODIFIED MM2 MODEL FOR THE RATES OF ACID-CATALYZED LACTONIZATIONS OF HYDROXY-ACIDS [J].

DORIGO, AE ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (12) :3698-3708

[8] EVIDENCE FOR A SINGLE TRANSITION-STATE IN THE INTERMOLECULAR TRANSFER OF A SULFONYL GROUP BETWEEN OXYANION DONOR AND ACCEPTORS [J].

DROZARIO, P ;

SMYTH, RL ;

WILLIAMS, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) :5027-5028

[9] 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

[10] 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

← 1 2 3 4 →