Conflicting evidence regarding the mechanism of the sulfonyl transfer reaction

被引：6

作者：

Hoz, S ^{[1
]}

Liu, P ^{[1
]}

Buncel, E ^{[1
]}

机构：

[1] QUEENS UNIV,DEPT CHEM,KINGSTON,ON K7L 3N6,CANADA

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 08期

关键词：

D O I：

10.1039/cc9960000995

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Application of the novel solvent-dependent pK(a) method for the construction of Bronsted-type plots to the sulfonyl transfer reaction with phenoxide nucleophiles, finds the pK(a)'s of aryloxides lower than those of the p-nitrophenoxide leaving group on separate lines, whereas nucleophiles of greater pK(a) fall on a common line, contrasting with the observed behaviour when using the traditional method.

引用

收藏

页码：995 / 996

页数：2

相关论文

共 23 条

[1] INTRINSIC BARRIERS OF REACTIONS AND THE PRINCIPLE OF NONPERFECT SYNCHRONIZATION [J].

BERNASCONI, CF .

ACCOUNTS OF CHEMICAL RESEARCH, 1987, 20 (08) :301-308

[2]

BERNASCONI CF, 1992, ADV PHYS ORG CHEM, V27, P119

[3] SOLVENT-INDEPENDENT TRANSITION-STATE STRUCTURE FOR ACYL-TRANSFER REACTIONS - A NOVEL STRATEGY FOR CONSTRUCTION OF A BRONSTED CORRELATION [J].

BUNCEL, E ;

UM, IH ;

HOZ, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (03) :971-975

[4] THE REACTIVITY SELECTIVITY PRINCIPLE - SHOULD IT EVER BE USED [J].

BUNCEL, E ;

WILSON, H .

JOURNAL OF CHEMICAL EDUCATION, 1987, 64 (06) :475-480

[5] THE PHENOMENOLOGY OF DIFFERENTLY CONSTRUCTED BRONSTED-TYPE PLOTS [J].

BUNCEL, E ;

TARKKA, R ;

HOZ, S .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (02) :109-110

[6]

BUNCEL E, 1977, ADV PHYS ORG CHEM, V14, P133

[7]

Cox B. G., 1975, FARADAY S CHEM SOC, V10, P107

[8] BRONSTED COEFFICIENTS AND SOLVENT EFFECTS [J].

COX, BG ;

GIBSON, A .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (16) :638-639

[9] 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

[10] NUCLEOPHILIC ATTACKS ON LOW LUMO COMPOUND .5. RADICAL-ANIONIC NATURE OF THE TRANSITION-STATE IN THE MICHAEL ADDITION-REACTION [J].

GROSS, Z ;

HOZ, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (22) :7489-7493