CORNER VERSUS EDGE PROTONATION OF CYCLOPROPANE

被引：13

作者：

BURRITT, A ^{[1
]}

COXON, JM ^{[1
]}

STEEL, PJ ^{[1
]}

机构：

[1] UNIV CANTERBURY,DEPT CHEM,CHRISTCHURCH 1,NEW ZEALAND

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 23期

关键词：

D O I：

10.1021/jo00128a046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acid-catalyzed addition of methanol to 1 occurs by rupture of the internal carbon-carbon bond of the cyclopropane to give 2 with both retention and inversion at the site of electrophilic attack (4:5, 1.3:1.0). Nucleophilic attack occurs with inversion without relaxation of the corner- and edge-protonated cyclopropanes to a secondary cation.

引用

收藏

页码：7670 / 7673

页数：4

相关论文

共 20 条

[1] DEUTERIUM-INDUCED NMR ISOTOPE SHIFTS FOR C-13 RESONANCE FREQUENCIES OF NORBORNANE - QUANTITATIVE DATA FOR THE DIHEDRAL ANGLE DEPENDENCE OF VICINAL SHIFTS [J].

AYDIN, R ;

FRANKMOLLE, W ;

SCHMALZ, D ;

GUNTHER, H .

MAGNETIC RESONANCE IN CHEMISTRY, 1988, 26 (05) :408-411

[2] CARBONIUM ION REARRANGEMENTS OF BICYCLO[2.2.2]OCT-2-YLCARBINYL DERIVATIVES [J].

BERSON, JA ;

LUIBRAND, RT ;

KUNDU, NG ;

MORRIS, DG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :3075-&

[3]

BLUNT JW, 1995, IN PRESS MAGN RESON

[4] BROMINATION OF EXO-TRICYCLO[3.2.1.0(2,4)]OCTANE AND ENDO-TRICYCLO[3.2.1.0(2,4)]OCTANE [J].

BURRITT, A ;

COXON, JM ;

STEEL, PJ ;

WHITTINGTON, BI .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2812-2819

[5]

Burritt A., 1993, TRENDS ORGANIC CHEM, V4, P517

[6]

BURRITT A, 1993, THESISU CANTERBURY C

[7] TRAJECTORY OF ELECTROPHILIC ATTACK ON TRISUBSTITUTED CYCLOPROPANES [J].

COXON, JM ;

STEEL, PJ ;

WHITTINGTON, BI .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) :4136-4144

[8] BROMINATION OF EXO-TRICYCLO[3.2.1.0(2,4)]OCT-6-ENE AND ENDO-TRICYCLO[3.2.1.0(2,4)]OCT-6-ENE [J].

COXON, JM ;

STEEL, PJ ;

BURRITT, A ;

WHITTINGTON, BI .

TETRAHEDRON, 1995, 51 (29) :8057-8072

[9] CORNER ATTACK ON EXO-TRICYCLO[3.2.1.0/2,4]OCTANE AND ENDO-TRICYCLO[3.2.1.0/2,4]OCTANE BY DEUTERON AND MERCURIC IONS [J].

COXON, JM ;

STEEL, PJ ;

WHITTINGTON, BI ;

BATTISTE, MA .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (06) :1383-1391

[10] CORNER ATTACK ON CYCLOPROPANE BY DEUTERON AND MERCURIC IONS - AN EXAMPLE OF STEREOSPECIFIC FORMATION AND CAPTURE OF UNSYMMETRICAL CORNER-DEUTERATED MERCURATED CYCLOPROPANE INTERMEDIATES [J].

COXON, JM ;

STEEL, PJ ;

WHITTINGTON, BI ;

BATTISTE, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (09) :2988-2990