Probing the ground-state δ effect of group 14 metal substituents.: X-ray structures of cis- and trans-4-trimethylmetal-substituted cyclohexyl p-nitrobenzenesulfonates

被引：4

作者：

Green, AJ ^{[1
]}

Van, V ^{[1
]}

White, JM ^{[1
]}

机构：

[1] Univ Melbourne, Sch Chem, Parkville, Vic 3052, Australia

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1998年 / 51卷 / 07期

关键词：

D O I：

10.1071/C98007

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Accurate low-temperature X-ray structural studies on trans-4-trimethylsilylcyclohexyl p-nitrobenzenesulfonate (31) and cis- and trans-4-trimethylstannylcyclohexyl p-nitrobenzenesulfonates (32) and (33) failed to demonstrate the presence of any significant structural effects due to a sigma(M-C)-sigma(C-C)sigma*(C-O) through-bond interaction between the C-M sigma donor orbital and the sigma*(C-ONs) acceptor orbital.

引用

页码：555 / 563

页数：9

共 30 条

[1] EVIDENCE FOR 2-FOLD HYPERCONJUGATION IN THE SOLVOLYSIS OF 5-(TRIMETHYLSILYL)-2-ADAMANTYL AND 5-(TRIMETHYLSTANNYL)-2-ADAMANTYL SULFONATES [J].

ADCOCK, W ;

COOPE, J ;

SHINER, VJ ;

TROUT, NA .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (05) :1411-1412

[2] THROUGH-BOND TRANSMISSION OF SUBSTITUENT EFFECTS IN THE BICYCLO[2.2.2]OCTANE RING-SYSTEM - SOLVOLYSIS OF 4-DEUTERIO (SI(CH3)3,GE(CH3)3,SN(CH3)3)-SUBSTITUTED AND 4-METALLOIDAL (SI(CH3)3,GE(CH3)3,SN(CH3)3)-SUBSTITUTED BICYCLO[2.2.2]OCT-1-YL PARA-NITROBENZENESULFONATES AND METHANESULFONATES [J].

ADCOCK, W ;

KRSTIC, AR ;

DUGGAN, PJ ;

SHINER, VJ ;

COOPE, J ;

ENSINGER, MW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3140-3145

[3] SUBSTITUENT EFFECTS IN THE BICYCLO[2.2.2]OCTANE RING-SYSTEM - A C-13 AND F-19 NUCLEAR MAGNETIC-RESONANCE STUDY OF 4-SUBSTITUTED BICYCLO[2.2.2]OCT-1-YL FLUORIDES [J].

ADCOCK, W ;

ABEYWICKREMA, AN .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (15) :2957-2966

[4] TRANSMISSION OF POLAR SUBSTITUENT EFFECTS IN THE ADAMANTANE RING-SYSTEM AS MONITORED BY F-19 NMR - HYPERCONJUGATION AS A STEREOINDUCTIVE FACTOR [J].

ADCOCK, W ;

TROUT, NA .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3229-3238

[5] Ground-state stereoelectronic effects involving silicon and germanium: A comparison of the effects of germanium and silicon substituents on C-O bond lengths at the beta-position [J].

Chan, VY ;

Clark, CI ;

Giordano, J ;

Green, AJ ;

Karalis, A ;

White, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5227-5233

[6]

Colvin E. W., 1981, BUTTERWORTHS MONOGRA

[7] GAMMA-SILICON STABILIZATION OF CARBONIUM-IONS [J].

DAVIDSON, ER ;

SHINER, VJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) :3135-3137

[8]

Egorochkin A.N., 1984, RUSS CHEM REV+, V53, P445, DOI [10.1070/RC1984v053n05ABEH003062, DOI 10.1070/RC1984V053N05ABEH003062]

[9]

ENSINGER MW, 1987, STUDIES ORGANIC CHEM, V31, P41

[10] SYNTHESIS AND CHARACTERIZATION OF CIS- AND TRANS- TRIMETHYLSILYLCYCLOHEXANOLS [J].

FESSENDEN, RJ ;

SEELER, K ;

DAGANI, M .

JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (08) :2483-+

← 1 2 3 →