Reactions of 1,4-dilithiobutadienes with isothiocyanates:: preparation of iminocyclopentadiene derivatives via cleavage of the C=S double bond of a RN=C=S molecule

被引：34

作者：

Wang, CY

Song, QL

Xi, ZF ^{[1
]}

机构：

[1] Peking Univ, Coll Chem, Minist Educ, Key Lab Bioorgan Chem & Mol Engn, Beijing 100871, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2004年 / 60卷 / 24期

基金：

中国国家自然科学基金;

关键词：

dilithio reagents; lsothiocyanates; iminocyclopentadienes;

D O I：

10.1016/j.tet.2004.04.045

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction patterns of 1,4-dilithio-butadiene derivatives with isothiocyanates RN=C=S and isocyanates RN=C=O were investigated and synthetically useful preparative methods were developed. Isothiocyanates reacted with 1,4-dilithio-butadienes to afford iminocyclopentadiene derivatives in excellent isolated yields and high selectivity. When aromatic isothiocyanates were used, cleavage of the C=S double bond of a RN C=S molecule took place via a successive inter-intramolecular carbophilic addition. A number of products were obtained from the reaction of isocyanates with 1,4-dilithio-butadienes, probably due to the high reactivity of isocyanates towards 1,4-dilithio-butadienes. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5207 / 5214

页数：8

共 58 条

[1] REACTIONS OF HETERONUCLEAR DIMETALLATED OLEFIN COMPLEXES - REACTIONS OF CPFE(CO)(2)[MU-(Z)-(MEO(2)C)C=C(CO(2)ME)]RE(CO)(4) WITH CO AND P-TOLYL ISOTHIOCYANATE [J].