The most stable methylcation. Tris(6-methoxy-1-azulenyl)methyl hexafluorophosphate

被引：16

作者：

Ito, S ^{[1
]}

Kikuchi, S ^{[1
]}

Morita, N ^{[1
]}

Asao, T ^{[1
]}

机构：

[1] IWATE UNIV, FAC EDUC, MORIOKA, IWATE 020, JAPAN

来源：

CHEMISTRY LETTERS | 1996年 / 02期

关键词：

D O I：

10.1246/cl.1996.175

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Extremely stable carbocations, tris(6-methoxy-1-azulenyl)methyl, bis(6-methoxy-1-azulenyl)(4-methoxyphenyl)methyl, and (6-methoxy-1-azulenyl)bis(4-methoxyphenyl)methyl cations were prepared and their pK(R+) values were determined spectrophotometrically as >14.0, >14.0, and 13.2, respectively. The extreme stability of these methyl cations are attributable to dipolar structures of azulene rings in addition to the contribution of mesomeric effect of three methoxy groups.

引用

收藏

页码：175 / 176

页数：2

相关论文

共 8 条

[1] SOLVENT EFFECTS IN ORGANIC CHEMISTRY .3. SOLVATION OF STABLE CARBONIUM + AMMONIUM IONS IN WATER . TEMPERATURE COEFFICIENT OF HR ACIDITY SCALE [J].

ARNETT, EM ;

BUSHICK, RD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (08) :1564-&

[2] SYNTHESIS AND DYNAMIC STEREOCHEMISTRY OF BIS (3-METHYL-1-AZULENYL)(1-NAPHTHYL)METHYL HEXAFLUOROPHOSPHATE - CLEAR EVIDENCE OF THE ONE-RING FLIP MECHANISM OF MOLECULAR PROPELLER BY CONTROLLING THE FLIPPING RING [J].

ITO, S ;

FUJITA, M ;

MORITA, N ;

ASAO, T .

CHEMISTRY LETTERS, 1995, (06) :475-476

[3] Synthesis and dynamic stereochemistry of di-1-azulenyl-(1- and 2-naphthyl)methyl hexafluorophosphates. Clear evidence of the one-ring flip mechanism of a molecular propeller by controlling the flipping ring [J].

Ito, S ;

Fujita, M ;

Morita, N ;

Asao, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (12) :3611-3620

[4] SYNTHESES OF AZULENE ANALOGS OF TRIPHENYLMETHYL CATION - EXTREMELY STABLE HYDROCARBON CARBOCATIONS AND THE FIRST EXAMPLE OF A ONE-RING FLIP AS THE THRESHOLD ROTATION MECHANISM FOR MOLECULAR PROPELLERS [J].

ITO, S ;

MORITA, N ;

ASAO, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1995, 68 (05) :1409-1436

[5] TRIS(3,6-DI-T-BUTYL-1-AZULENYL)METHYL CATION - HYDROCARBON CATION WITH THE HIGHEST PK(R)(+) VALUE [J].

ITO, S ;

MORITA, N ;

ASAO, T .

TETRAHEDRON LETTERS, 1994, 35 (05) :751-754

[6] AZULENE ANALOGS OF TRIPHENYLMETHYL CATION - EXTREMELY STABLE HYDROCARBON CARBOCATIONS [J].

ITO, S ;

MORITA, N ;

ASAO, T .

TETRAHEDRON LETTERS, 1991, 32 (06) :773-776

[7] 1,2-3,4-5,6-TRIS(BICYCLO[2.2.2]OCTENO)TROPYLIUM ION - AN ALL-HYDROCARBON CARBOCATION WITH EXTRAORDINARY STABILITY [J].

KOMATSU, K ;

AKAMATSU, H ;

JINBU, Y ;

OKAMOTO, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (02) :633-634

[8]

YOSHIDA Z, 1973, TETRAHEDRON LETT, P869