THE SUBSTITUENT EFFECT OF A BETA-CARBON-OXYGEN BOND IN RADICAL REACTIONS

被引：12

作者：

ROBERTS, BP

STEEL, AJ

机构：

[1] Christopher Ingold Laboratories, Department of Chemistry, University College London, London, WC1H OAJ

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 32期

关键词：

D O I：

10.1016/S0040-4039(00)60704-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rates of chlorine-atom abstraction by Me3N-->BHBu and Et3Si. from RCH2Cl [R = Pr, MeOCH2, (MeO)2CH, Me3Si] have been determined using ESR spectroscopy. The relatively rapid abstraction of chlorine from MeOCH2CH2Cl by the very nucleophilic Me3N-->BHBu is attributed to a kinetic anomeric effect.

引用

收藏

页码：5167 / 5170

页数：4

相关论文

共 21 条

[1] OXYGEN CARBON BETA-BOND EFFECTS IN RADICAL REACTIONS [J].

BARTON, DHR ;

HARTWIG, W ;

MOTHERWELL, WB .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (08) :447-448

[2] AN ELECTRON-SPIN RESONANCE INVESTIGATION OF FREE-RADICALS WITH OXYGEN-CONTAINING AND SULFUR-CONTAINING SUBSTITUENTS [J].

BECKWITH, ALJ ;

BRUMBY, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :1801-1807

[3] SUBSTITUENT EFFECTS IN BRIDGING BY OXYGEN IN ALKYL RADICALS BY ELECTRON-SPIN RESONANCE [J].

CHEN, KS ;

KOCHI, JK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (05) :1383-1392

[4] A RELIABLE AND INEXPENSIVE METHOD FOR CALCULATING IONIZATION-POTENTIALS AND ELECTRON-AFFINITIES OF RADICALS AND MOLECULES [J].

DANOVICH, D ;

APELOIG, Y ;

SHAIK, S .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (03) :321-330

[5] HOMOLYTIC ORGANOMETALLIC REACTIONS .3. ELECTRON SPIN RESONANCE STUDY OF HOMOLYTIC TERT-BUTOXYDEALKYLATION OF ORGANOMETALLIC COMPOUNDS - RATE CONSTANTS FOR REACTION AT BORON [J].

DAVIES, AG ;

GRILLLER, D ;

ROBERTS, BP .

JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (09) :1823-&

[6] EPR STUDIES OF THE ADDITION OF 1,1-BIS(ALKOXYCARBONYL)ALKYL RADICALS AND TRIS(ETHOXYCARBONYL)METHYL RADICALS TO ALKENES AND TO ALKYL ISOCYANIDES [J].

DIART, V ;

ROBERTS, BP .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (10) :1761-1768

[7] ELECTRON-SPIN RESONANCE STUDIES .32. INFORMATION FROM HYPERFINE SPLITTINGS FOR ALIPHATIC RADICALS ABOUT SHAPE AND CONFORMATION [J].

DOBBS, AJ ;

GILBERT, BC ;

NORMAN, ROC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1972, (06) :786-&

[8] CONFORMATION OF GLYCOSYL RADICALS - RADICAL STABILIZATION BY BETA-CO BONDS [J].

DUPUIS, J ;

GIESE, B ;

RUEGGE, D ;

FISCHER, H ;

KORTH, HG ;

SUSTMANN, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (11) :896-898

[9]

Fleming I., 1976, FRONTIER ORBITALS OR, pCH5

[10] INVESTIGATIONS OF STRUCTURE AND CONFORMATION .4. ELECTRON-SPIN RESONANCE AND INDO MOLECULAR-ORBITAL STUDY OF INFLUENCE OF ELECTRONIC INTERACTIONS UPON RADICAL GEOMETRY [J].

GILBERT, BC ;

TRENWITH, M ;

DOBBS, AJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1974, (15) :1772-1779