TRIMETHYLSILYLKETENE - REACTIVITY AND STABILIZATION

被引:28
作者
ALLEN, AD [1 ]
TIDWELL, TT [1 ]
机构
[1] UNIV TORONTO, DEPT CHEM, TORONTO M5S 1A1, ONTARIO, CANADA
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/S0040-4039(00)92101-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Me3SiCH = C = O is stable thermally, and is less reactive than t-BuCH = C = O toward H2O in neutral hydration, but in acid and base induced hydrations the reactivity is accelerated relative to alkylketenes. The contrasting reactivities are due to the relative degree of silicon stabilization of the ground state and the different transition states.
引用
收藏
页码:847 / 850
页数:4
相关论文
共 36 条
  • [1] KINETICS AND MECHANISM OF HYDRATION OF ALKYLKETENES
    ALLEN, AD
    TIDWELL, TT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) : 2774 - 2780
  • [2] CONJUGATED KETENES - CYCLOPROPYL, ALKENYL, ALKYNYL, AND ACYL SUBSTITUENTS
    ALLEN, AD
    GONG, L
    TIDWELL, TT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) : 6396 - 6397
  • [3] HYDRATION REACTIVITY OF PERSISTENT CONJUGATED KETENES
    ALLEN, AD
    STEVENSON, A
    TIDWELL, TT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) : 2843 - 2848
  • [4] HYDRATION REACTIVITY OF KETENES GENERATED BY FLASH-PHOTOLYSIS
    ALLEN, AD
    KRESGE, AJ
    SCHEPP, NP
    TIDWELL, TT
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 1987, 65 (08) : 1719 - 1723
  • [5] STEREOSPECIFIC FORMATION OF ENOLATES FROM REACTION OF UNSYMMETRICAL KETENES AND ORGANO-LITHIUM REAGENTS
    BAIGRIE, LM
    SEIKLAY, HR
    TIDWELL, TT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) : 5391 - 5396
  • [6] BASSINDALE AR, 1989, CHEM ORGANIC SILICON, pCH14
  • [7] REACTION OF (TRIMETHYLSILYL)KETENE WITH SILYLATED KETENE ACETALS
    BRADY, WT
    SAIDI, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (13) : 4215 - 4216
  • [8] BRADY WT, 1976, TETRAHEDRON LETT, P1553
  • [9] EFFECT OF TRIMETHYLSILYLMETHYL SUBSTITUENT ON KETENE CYCLOADDITIONS
    BRADY, WT
    CHENG, TC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) : 732 - 734
  • [10] TRIMETHYLSILYLKETENE - CYCLOADDITIONS OF KETENES AND ALDEHYDES
    BRADY, WT
    SAIDI, K
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (05) : 733 - 737