THE NATURE OF ELECTRONIC INTERACTIONS GOVERNING THE CONTROL OF PI-FACIAL SELECTIVITY IN THE CAPTURE OF 5-SUBSTITUTED(X)-2-ADAMANTYL RADICALS - ELECTROSTATIC VERSUS HYPERCONJUGATIVE EFFECTS

被引：19

作者：

ADCOCK, W

CLARK, CI

TROUT, NA

机构：

[1] School of Physical Sciences, The Flinders University of South Australia, Adelaide

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 02期

关键词：

D O I：

10.1016/S0040-4039(00)76536-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An electrostatic rather than a hyperconjugative effect appears to be the dominant factor governing the control of Pi-facial selectivity in the capture of 5-substituted(X)-2-adamantyl radicals.

引用

页码：297 / 300

页数：4

共 18 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] MECHANISTIC DEFINITION OF TRIMETHYLSTANNYLATION OF 1,4-DIHALOBICYCLO[2.2.2]OCTANES - A LABELING EXPERIMENT EXCLUDES INTERMEDIACY OF [2.2.2]PROPELLANE BUT SUGGESTS A NOVEL RADICAL CHAIN MECHANISM [J].

ADCOCK, W ;

IYER, VS ;

KITCHING, W ;

YOUNG, D .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3706-3710

[3] 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

[4] F-19 NUCLEAR MAGNETIC-RESONANCE STUDIES OF 4-SUBSTITUTED BICYCLO[2.2.2]OCT-1-YL FLUORIDES - RESONANCE EFFECTS OF SOME GROUP-14 SUBSTITUENTS ATTACHED TO SATURATED CARBON CENTERS [J].

ADCOCK, W ;

IYER, VS .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (09) :1538-1540

[5] 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

[6] 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

[7]

ADCOCK W, 1980, J ORGANOMET CHEM, V202, P395

[8]

ADCOCK W, UNPUB J ORG CHEM

[9] ELECTRONIC CONTROL OF FACE SELECTION IN THE CAPTURE OF RADICALS [J].

BODEPUDI, VR ;

LENOBLE, WJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) :2001-2006

[10]

CIEPLAK AS, 1981, J AM CHEM SOC, V103, P4540, DOI 10.1021/ja00405a041

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