ORIGINS OF THE REGIOSELECTIVITY OF CYCLOPROPYLCARBINYL RING-OPENING REACTIONS IN BICYCLO [N.1.0] SYSTEMS

被引：23

作者：

BATEY, RA ^{[1
]}

GRICE, P ^{[1
]}

HARLING, JD ^{[1
]}

MOTHERWELL, WB ^{[1
]}

RZEPA, HS ^{[1
]}

机构：

[1] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1992年 / 13期

关键词：

D O I：

10.1039/c39920000942

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Addition of .CCl3 radicals to sabinene 1 (R1 = Pr(i)) and a related bicyclo [4.1.0] derivative in BrCCl3 results in kinetic trapping of the exo ring opened intermediate but in CCl4 as solvent the major products are derived from the thermodynamically more stable endo radical; the radical and cationic regioselectivities are related to the features of a PM3 SCF-MO orbital correlation diagram.

引用

页码：942 / 944

页数：3

共 26 条

[1] SPECIFIC BETA-SCISSION OF 3BETA,5-CYCLOCHOLESTAN-6-YL RADICAL [J].

BECKWITH, ALJ ;

PHILLIPOU, G .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (01) :123-131

[2]

CLISSE JA, 1970, J CHEM SOC C, P258

[3] SEQUENTIAL RADICAL RING-CLOSURE RADICAL RING-OPENING - USE IN THE PREPARATION OF BENZOFURANS [J].

CLIVE, DLJ ;

DAIGNEAULT, S .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (18) :5285-5289

[4] HOMOALLYLIC FREE RADICALS . A STUDY OF REARRANGEMENT OF 3,5-CYCLOCHOLESTANYL RADICAL TO CHOLESTERYL RADICAL [J].

CRISTOL, SJ ;

BARBOUR, RV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (11) :2832-+

[5] 2-ACYL THIAZOLIUM SALTS AS SELECTIVE AGENTS FOR THE O-ACYLATION OF AROMATIC HYDROXYLAMINES [J].

FERREIRA, LM ;

LOBO, AM ;

PRABHAKAR, S ;

MARCELOCURTO, MJ ;

RZEPA, HS ;

YI, MY .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (16) :1127-1128

[6] SOLVOLYTIC STUDIES IN 2-BICYCLO[3.1.0]HEXYL SYSTEM [J].

FRIEDRIC.EC ;

SALEH, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (08) :2617-2623

[7] CYCLOPROPYLCARBINYL-ALLYLCARBINYL RADICAL REARRANGEMENTS IN BENZOBICYCLO[4.1.0]HEPTENE SYSTEM [J].

FRIEDRICH, EC ;

HOLMSTEA.RL .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (16) :2546-+

[8] CYCLOPROPYLCARBINYL RADICAL REACTIONS IN CYCLOPROP[2,3]INDENE SYSTEM [J].

FRIEDRICH, EC ;

HOLMSTEA.RL .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (07) :971-+

[9] CYCLOPROPYLCARBINYL-ALLYLCARBINYL RADICAL REARRANGEMENTS IN SIMPLE BICYCLO[3.1.0)HEXYL AND BICYCLO[4.1.0]HEPTYL SYSTEMS [J].

FRIEDRICH, EC ;

HOLMSTEA.RL .

JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (16) :2550-+

[10] METHYL SUBSTITUENT EFFECTS UPON THE CHEMISTRY OF 2-BICYCLO[4.1.0]HEPTYL 3,5-DINITROBENZOATES [J].

FRIEDRICH, EC ;

JASSAWALLA, JDC .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) :4224-4229

← 1 2 3 →