2-vinyl-1,1,2-trihalocyclopropanes - Valuable five carbon cyclopropane and cyclopropene synthetic intermediates

被引：13

作者：

AlDulayymi, AR

Baird, MS

机构：

[1] Department of Chemistry, University of Wales, Bangor

来源：

TETRAHEDRON | 1996年 / 52卷 / 33期

关键词：

D O I：

10.1016/0040-4020(96)00592-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The dichloro- and dibromocarbene adducts of chloroprene and 2,3-dichlorobutadiene are readily dehalogenated by reaction with methylithium to give 1-halo-2-vinylcyclopropenes which on further lithium-halogen exchange give synthetically useful 1-lithio-2-vinylcyclopropenes. Trapping of 1-lithio-2-(1-chlorovinyl)cyclopropene with methyl chloroformate leads to a very unusual cyclononadienyne. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：10955 / 10968

页数：14

共 18 条

[1] 1,2,2-tribromocyclopropanecarboxylic acid and derivatives - Valuable intermediates for four carbon cyclopropane and cyclopropene synthons [J].

AlDulayymi, AR ;

AlDulayymi, JR ;

Baird, MS ;

Gerrard, ME ;

Koza, G ;

Harkins, SD ;

Roberts, E .

TETRAHEDRON, 1996, 52 (10) :3409-3424

[2]

APELIOG Y, 1987, TETRAHEDRON LETT, P5917

[3]

BAIR MS, UNPUB

[4] THE PREPARATION AND LITHIATION OF 1-HALOGENOCYCLOPROPENES [J].

BAIRD, MS ;

HUSSAIN, HH ;

NETHERCOTT, W .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (10) :1845-1853

[5]

BAIRD MS, 1991, ADV STRAIN ORGANIC C, V1, P65

[6]

BAIRD MS, CARBOCYCLIC 3 RING E, V17

[7] USES OF ADSORBED REAGENTS IN THE SYNTHESIS OF REACTIVE MOLECULES VIA ELIMINATION-REACTIONS [J].

BILLUPS, WE ;

LIN, LJ .

TETRAHEDRON, 1986, 42 (06) :1575-1579

[8] 1,3-ADDITION OF TERT-BUTYLMAGNESIUM CHLORIDE TO ETHYL CINNAMATE - UNPRECEDENTED COURSE OF REACTION [J].

CROSSLAND, I .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1975, 29 (04) :468-470

[9]

DIETRICHBUCHECK.C, 1980, TETRAHEDRON LETT, P671

[10]

DYAKONOV IA, 1967, ZH ORG KHIM, V3, P273

← 1 2 →