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

被引:12
作者
AlDulayymi, AR
Baird, MS
机构
[1] Department of Chemistry, University of Wales, Bangor
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
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页码:10955 / 10968
页数:14
相关论文
共 18 条
  • [1] 1,2,2-tribromocyclopropanecarboxylic acid and derivatives - Valuable intermediates for four carbon cyclopropane and cyclopropene synthons
    AlDulayymi, AR
    AlDulayymi, JR
    Baird, MS
    Gerrard, ME
    Koza, G
    Harkins, SD
    Roberts, E
    [J]. 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
    BAIRD, MS
    HUSSAIN, HH
    NETHERCOTT, W
    [J]. 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
    BILLUPS, WE
    LIN, LJ
    [J]. TETRAHEDRON, 1986, 42 (06) : 1575 - 1579
  • [8] 1,3-ADDITION OF TERT-BUTYLMAGNESIUM CHLORIDE TO ETHYL CINNAMATE - UNPRECEDENTED COURSE OF REACTION
    CROSSLAND, I
    [J]. 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