Rapid-injection NMR study of lodo- and cyano-gilman reagents with 2-cyclohexenone:: observation of π-complexes and their rates of formation1

被引：51

作者：

Bertz, SH ^{[1
]}

Carlin, CM

Deadwyler, DA

Murphy, MD

Ogle, CA

Seagle, PH

机构：

[1] Complex Study Ctr, Mendham, NJ 07945 USA

[2] Univ N Carolina, Dept Chem, UNCC Stn, Charlotte, NC 28223 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2002年 / 124卷 / 46期

关键词：

D O I：

10.1021/ja027744s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rapid-injection is a very useful technique for the preparation of temperature-sensitive and air-sensitive compounds in the cold, nitrogen-filled probe of an NMR spectrometer. We have used this method to prepare solutions of π-complexes from 2-cyclohexenone and prototypical cuprates Me2CuLi·LiI and Me2CuLi·LiCN, and we have assigned structures on the basis of 1H and 13C NMR. In each case two π-complexes were observed, and in the former, their rates of formation were measured by rapid-injection 1H NMR and EXSY spectroscopy. These results provide insights into the normal and anomalous conjugate addition reactions of organocuprates. Copyright © 2002 American Chemical Society.

引用

页码：13650 / 13651

页数：2

共 29 条

[1] DIRECT MICHAEL ADDITIONS OF SILYL GROUPS TO ALPHA,BETA-UNSATURATED BETA-ARYLKETONES AND AN ALPHA-BENZYLIDENELACTONE WITH MIXTURES OBTAINED FROM COPPER(I) CYANIDE, BUTYLLITHIUM AND CHLOROSILANES [J].