Synthesis of (Z)- and (E)-1,2-di(1-adamantyl)ethene and their respective reactions with dichlorocarbene

被引：11

作者：

Marchand, AP

Xing, DX

Bott, SG

机构：

[1] Department of Chemistry, University of North Texas, Denton

来源：

TETRAHEDRON | 1996年 / 52卷 / 03期

关键词：

(Z)- and (E)-1,2-Di(1-adamantyl)ethene; dichloro carbene; carbon-hydrogen bond insertion;

D O I：

10.1016/0040-4020(95)00934-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of (Z)- and (E)-1,2-di(I-adamantyl)ethene (la and Ib, respectively) is reported. Compound la reacts with dichlorocarbene to afford (Z)-1-[3-(dichloromethyl)-1-adamantyl],2-(1-adamantyl)ethene (2, 27%), (Z)-2,3-dichloro-1,3-di(l-adamantyl)propene (3, 20%) and 1,1,2-trichloro-2-(1-adamantyl)chloromethyl-3-(l-adamantyl)cyclopropane (4, 21%). The corresponding reaction of Ib produced (E)-1-[3-(dichloromethyl)-1-adamantyl],2-(1-adamantyl)ethene (5, 34%) and (E)-1,2-di[3-(dichloromethyl)-1-adamantyl]ethene (6, 5%). The structures of 6, 7, and 10 were established unequivocally via application of X-ray crystallographic methods.

引用

页码：825 / 832

页数：8

共 26 条

[1] BETA-LACTONES AS CONVENIENT PRECURSORS TO STERICALLY CONGESTED OLEFINS [J].