MECHANISM OF CONJUGATE ADDITIONS OF DIALKYLCUPRATES TO BROMONAPHTHOQUINONES

被引:18
作者
WIGAL, CT [1 ]
GRUNWELL, JR [1 ]
HERSHBERGER, J [1 ]
机构
[1] MIAMI UNIV, DEPT CHEM, OXFORD, OH 45056 USA
关键词
D O I
10.1021/jo00012a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The correlation of bromonaphthoquinone redox potentials with reactivity toward dialkylcuprates reveals that the conjugate addition of Gilman reagents to bromojuglones proceeds via a single-electron-transfer mechanism.
引用
收藏
页码:3759 / 3761
页数:3
相关论文
共 13 条
[1]   ELECTRON-SPIN-RESONANCE STUDIES OF FREE-RADICALS DERIVED FROM HYDROXYQUINONES .1. GROUP-14 ADDUCTS OF HYDROXYNAPHTHOQUINONES [J].
AHMED, IM ;
HUDSON, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1987, 333 (01) :9-16
[3]   REACTION OF BU2CULI.LII WITH ALKYL IODIDES - EVIDENCE FOR FREE-RADICALS AND ELECTRON-TRANSFER [J].
BERTZ, SH ;
DABBAGH, G ;
MUJSCE, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :631-636
[4]   ADDITION OF ME2CULI TO ORTHO-SUBSTITUTED METHYL CINNAMATES - AN NMR-STUDY OF THE PI-COMPLEX FORMATION [J].
CHRISTENSON, B ;
OLSSON, T ;
ULLENIUS, C .
TETRAHEDRON, 1989, 45 (02) :523-534
[5]   GROUND-STATES OF MOLECULES .38. MNDO METHOD - APPROXIMATIONS AND PARAMETERS [J].
DEWAR, MJS ;
THIEL, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (15) :4899-4907
[6]   Synthesis of plumbagin [J].
Fieser, LF ;
Dunn, JT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1936, 58 :572-575
[7]   THE FORMAL OXIDATIVE ADDITION OF ELECTRON-RICH TRANSOID DIENES TO BROMONAPHTHOQUINONES [J].
GRUNWELL, JR ;
KARIPIDES, A ;
WIGAL, CT ;
HEINZMAN, SW ;
PARLOW, J ;
SURSO, JA ;
CLAYTON, L ;
FLEITZ, FJ ;
DAFFNER, M ;
STEVENS, JE .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) :91-95
[8]   REACTIONS INVOLVING ELECTRON-TRANSFER .3. CONJUGATE ADDITION OF LITHIUM DIMETHYLCUPRATE TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
HOUSE, HO ;
UMEN, MJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (15) :5495-&
[9]   CHEMISTRY OF CARBANIONS .12. ROLE OF COPPER INCONJUGATE ADDITION OF ORGANOMETALLIC REAGENTS [J].
HOUSE, HO ;
RESPESS, WL ;
WHITESID.GM .
JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (10) :3128-&
[10]   SELF-CONSISTENT FIELD THEORY OF THE ELECTRON SPIN DISTRIBUTION IN PI-ELECTRON RADICALS [J].
MCLACHLAN, AD .
MOLECULAR PHYSICS, 1960, 3 (03) :233-252