METHYLENE PHOSPHONIUM IONS

被引:57
作者
GRUTZMACHER, H
PRITZKOW, H
机构
[1] Anorganisch-Chemisches Institut, Universität Heidelberg, Heidelberg, W-6900
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1991年 / 30卷 / 06期
关键词
D O I
10.1002/anie.199107091
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Despite steric shielding of the P = C bond, the methylenephosphonium ions 1 and 2 react with 2,3-dimethylbutadiene in an ene reaction and a [2 + 4]cyclo-addition reaction, respectively, to give 3 and 4 (counterion in all cases AlCl4-). This reaction behavior is understandable from the pronounced electron-deficient character of the alkyl-substituted P atoms. Compounds 1 and 2 are formed in high yields from the corresponding P-chloro-substituted phosphorus ylides by chloride abstraction.
引用
收藏
页码:709 / 710
页数:2
相关论文
共 18 条
  • [1] PHOSPHORUS-CARBON-HALOGEN COMPOUNDS .34. P-CHLOROMETHYLENEPHOSPHORANES
    APPEL, R
    SCHMITZ, R
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1983, 116 (10): : 3521 - 3523
  • [2] GENERAL REACTION OF PHOSPHINES AND CARBON-TETRACHLORIDE ON NUCLEOPHILES .29. REACTIONS IN SYSTEM TRIPHENYLPHOSPHINE-CARBON TETRACHLORIDE
    APPEL, R
    KNOLL, F
    MICHEL, W
    MORBACH, W
    WIHLER, HD
    VELTMANN, H
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (01): : 58 - 70
  • [3] BROOK AG, 1990, HETEROATOM CHEMISTRY /, P105
  • [4] EHRIG M, IN PRESS J AM CHEM S
  • [5] GRUTZMACHER HF, UNPUB
  • [6] SYNTHESIS, REACTIVITY, AND CRYSTAL-STRUCTURE OF THE 1ST METHYLENEPHOSPHONIUM ION - A SEVERELY TWISTED VALENCE ISOELECTRONIC OLEFIN
    IGAU, A
    BACEIREDO, A
    GRUTZMACHER, H
    PRITZKOW, H
    BERTRAND, G
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) : 6853 - 6854
  • [7] CARBOSILYLATED PHOSPHA-ALKENES
    ISSLEIB, K
    SCHMIDT, H
    WIRKNER, C
    [J]. ZEITSCHRIFT FUR ANORGANISCHE UND ALLGEMEINE CHEMIE, 1981, 473 (02): : 85 - 90
  • [8] KOLODIAZNYI OI, 1989, Z CHEM, V29, P396
  • [9] KOLODYAZHNYI OI, 1981, ZH OBSHCH KHIM+, V51, P2466
  • [10] SUBSTITUTION AND ADDITION-REACTIONS OF A METHYLENEPHOSPHINE WITH ALKYLLITHIUM REAGENTS
    LI, BL
    NEILSON, RH
    [J]. INORGANIC CHEMISTRY, 1984, 23 (22) : 3665 - 3666