9-(TRIFLUOROMETHYL)FLUORENYL CATION - A NEW DOUBLY DESTABILIZED CARBOCATION

被引：40

作者：

ALLEN, AD

COLOMVAKOS, JD

TEE, OS

TIDWELL, TT

机构：

[1] UNIV TORONTO,DEPT CHEM,TORONTO M5S 1A1,ON,CANADA

[2] CONCORDIA UNIV,DEPT CHEM & BIOCHEM,MONTREAL H3G 1M8,PQ,CANADA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 24期

关键词：

D O I：

10.1021/jo00103a001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

9-(Trifluoromethyl)fluorenyl tosylate (5) undergoes solvolysis to the corresponding carbocation 3, which is destabilized both by the electron-withdrawing CF3 group and by its potentially antiaromatic fluorenyl cation character.

引用

页码：7185 / 7187

页数：3

共 35 条

[1] SOLVOLYTIC REACTIVITY OF 1-TRIFLUOROMETHYL-1-PHENYLETHYL TOSYLATE - FORMATION OF A HIGHLY DESTABILIZED CARBONIUM-ION [J].

ALLEN, AD ;

JANSEN, MP ;

KOSHY, KM ;

MANGRU, NN ;

TIDWELL, TT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (01) :207-211

[2] DOUBLY DESTABILIZED CARBOCATIONS - STRONG ARYL DELOCALIZATION AND THE ATTENUATION OF RATE DECELERATING EFFECTS OF CF3 AND CN GROUPS [J].

ALLEN, AD ;

KANAGASABAPATHY, VM ;

TIDWELL, TT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3470-3474

[3] LARGE SALT EFFECTS AND ION-PAIRING IN TRIFLUOROACETOLYSIS FORMING DESTABILIZED DELOCALIZED BENZYLIC CARBOCATIONS - KINETIC-ANALYSIS OF THE WINSTEIN SPECIAL SALT EFFECT [J].

ALLEN, AD ;

TIDWELL, TT ;

TEE, OS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (22) :10091-10096

[4]

ALLEN AD, 1989, ADV CARBOCATION CHEM, V1, P1

[5] EXPERIMENTS AND CALCULATIONS FOR DETERMINATION OF THE STABILITIES OF BENZYL, BENZHYDRYL, AND FLUORENYL CARBOCATIONS - ANTIAROMATICITY REVISITED [J].

AMYES, TL ;

RICHARD, JP ;

NOVAK, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8032-8041

[6] DESTABILIZED VINYL CATIONS - AN MO STUDY OF THE INFLUENCE OF ELECTRON-WITHDRAWING SUBSTITUENTS [J].

APELOIG, Y ;

BITON, R ;

ZUILHOF, H ;

LODDER, G .

TETRAHEDRON LETTERS, 1994, 35 (02) :265-268

[7] IMPORTANCE OF ELECTRONIC GEMINAL INTERACTIONS IN SOLVOLYSIS REACTIONS - APPLICATION TO THE DETERMINATION OF THE ALPHA-SILYL EFFECT ON CARBENIUM ION STABILITY [J].

APELOIG, Y ;

BITON, R ;

ABUFREIH, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (06) :2522-2523

[8] ANTIAROMATICITY [J].

BRESLOW, R .

ACCOUNTS OF CHEMICAL RESEARCH, 1973, 6 (12) :393-398

[9] HYDRIDE AFFINITIES OF CARBENIUM IONS IN ACETONITRILE AND DIMETHYL-SULFOXIDE SOLUTION [J].

CHENG, JP ;

HANDOO, KL ;

PARKER, VD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (07) :2655-2660

[10] REACTIVITY IN NUCLEOPHILIC SUBSTITUTION .3. ACETOLYSIS OF 9-FLUORENYL TOULENE-P-SULPHONATE [J].

COWELL, GW ;

LEDWITH, A .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1967, (07) :695-&

← 1 2 3 4 →