SOLVOLYTIC REACTIVITY OF 1-TRIFLUOROMETHYL-1-PHENYLETHYL TOSYLATE - FORMATION OF A HIGHLY DESTABILIZED CARBONIUM-ION

被引:69
作者
ALLEN, AD [1 ]
JANSEN, MP [1 ]
KOSHY, KM [1 ]
MANGRU, NN [1 ]
TIDWELL, TT [1 ]
机构
[1] UNIV TORONTO,SCARBOROUGH COLL,DEPT CHEM,W HILL M1C 1A4,ONTARIO,CANADA
关键词
D O I
10.1021/ja00365a037
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:207 / 211
页数:5
相关论文
共 53 条
[1]  
BEGUE JP, 1980, ACCOUNTS CHEM RES, V13, P207, DOI 10.1021/ar50151a003
[2]  
Bentley T.W., 1977, ADV PHYS ORG CHEM, V14, P32
[3]   THE SN2-SN1 SPECTRUM .3. SOLVOLYSES OF SECONDARY AND TERTIARY ALKYL SULFONATES IN FLUORINATED ALCOHOLS - FURTHER EVIDENCE FOR THE SN2 (INTERMEDIATE) MECHANISM [J].
BENTLEY, TW ;
BOWEN, CT ;
MORTEN, DH ;
SCHLEYER, PV .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5466-5475
[4]   EVIDENCE AGAINST APPRECIABLE INTERNAL ION-PAIR RETURN IN THE SOLVOLYSES OF TERTIARY ALIPHATIC HALIDES - MEASUREMENT OF ALPHA-METHYL-HYDROGEN RATE RATIOS IN HEXAFLUOROPROPAN-2-OL-WATER [J].
BENTLEY, TW ;
BOWEN, CT ;
PARKER, W ;
WATT, CIF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1980, (08) :1244-1252
[5]   HYDROLYSIS OF SECONDARY ALKYL SULFONATES - SN2 REACTIONS WITH HIGH CARBOCATION CHARACTER [J].
BENTLEY, TW ;
BOWEN, CT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (06) :557-562
[6]  
BENTLEY TW, 1977, ADV PHYS ORG CHEM, V14, P29
[7]   STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .19. RELATIVE ELECTRON RELEASING CAPABILITY OF METHYL, PHENYL, AND CYCLOPROPYL GROUPS AS MEASURED BY TOOL OF INCREASING ELECTRON DEMAND [J].
BROWN, HC ;
RAVINDRANATHAN, M ;
PETERS, EN .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (06) :1073-1076
[8]   STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .26. CRITICAL STUDY OF EFFECT OF SOLVENT ON EXO-ENDO RATE RATIO IN SOLVOLYSIS OF 2-NORBORNYL DERIVATIVES - EVIDENCE THAT EXO-ENDO RATE RATIO IS NOT RESULT OF K-DELTA-K-S PROCESSES [J].
BROWN, HC ;
RAVINDRANATHAN, M ;
CHLOUPEK, FJ ;
ROTHBERG, I .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (10) :3143-3149
[9]   GENERATION OF ALPHA-KETO CATIONS - QUANTITATIVE ASPECTS [J].
CREARY, X .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (22) :3938-3945
[10]   STABILIZATION OF ALPHA-KETO CATIONS BY CARBONYL CONJUGATION [J].
CREARY, X .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) :2463-2465