PHOTO-CHEMICAL DECOMPOSITION OF TRIMETHYLSILYL DIAZOACETATES IN ALCOHOLS

被引:28
作者
ANDO, W
SEKIGUCHI, A
HAGIWARA, T
MIGITA, T
CHOWDHRY, V
WESTHEIMER, FH
KAMMULA, SL
GREEN, M
JONES, M
机构
[1] HARVARD UNIV,CAMBRIDGE,MA 02136
[2] GUNMA UNIV,KIRYU,GUNMA,JAPAN
[3] PRINCETON UNIV,PRINCETON,NJ 08544
关键词
D O I
10.1021/ja00515a038
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Photolysis of trimethylsilylcarboalkoxy diazoacetates in alcohols yields the products of insertion of the corresponding carbenes into the O-H bond, compounds derived from Wolff rearrangement, and the compounds most simply attributed to trapping of silenes. However, in the gas phase the immediate precursor to this third type of compound is not the silene but rather a dimethylalkoxysilylketene. The source of this ketene is discussed. Dimethylphenylsilylcarboalkoxycarbene is shown to yield a similar ketene very efficiently. Reactions of trimethylsilylcarbene and of phenyltrimethylsilylcarbene in alcohols are also described. © 1979, American Chemical Society. All rights reserved.
引用
收藏
页码:6393 / 6398
页数:6
相关论文
共 24 条
  • [1] GAS-PHASE PYROLYSIS OF PHENYLTRIMETHYLSILYLDIAZOMETHANE - INTRAMOLECULAR CHEMISTRY OF PHENYLTRIMETHYLSILYLCARBENE
    ANDO, W
    SEKIGUCHI, A
    ROTHSCHILD, AJ
    GALLUCCI, RR
    JONES, M
    BARTON, TJ
    KILGOUR, JA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (21) : 6995 - 6999
  • [2] PHOTOLYSIS OF SILYLDIAZOMETHANE - MIGRATING TENDENCIES OF GROUPS ON SILICON ATOM
    ANDO, W
    SEKIGUCHI, A
    MIGITA, T
    [J]. CHEMISTRY LETTERS, 1976, (07) : 779 - 782
  • [3] FORMATION OF AN UNSTABLE SILICON-CARBON DOUBLE-BOND IN PHOTODECOMPOSITION OF TRIMETHYLSILYLDIAZOACETATE
    ANDO, W
    HAGIWARA, T
    MIGITA, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (22) : 7518 - 7519
  • [4] ROLE OF ALKOXYSILYLKETENES AND ABSENCE OF CARBON-SILICON DOUBLE-BONDS IN GAS-PHASE DECOMPOSITION OF TRIMETHYLSILYLDIAZOACETATES
    ANDO, W
    SEKIGUCHI, A
    MIGITA, T
    KAMMULA, S
    GREEN, M
    JONES, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (13) : 3818 - 3819
  • [5] ANDO W, 1978, CHEM DIAZONIUM DIA 1, pCH9
  • [6] ANDO W, UNPUBLISHED
  • [7] SYNTHESIS OF SILYL- AND GERMYLDIAZOALKANES VIA TOSYLHYDRAZONES
    BROOK, AG
    JONES, PF
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 1969, 47 (23): : 4353 - &
  • [8] 1,1,2-TRIMETHYLSILAETHYLENE
    CHAPMAN, OL
    CHANG, CC
    KOLC, J
    JUNG, ME
    LOWE, JA
    BARTON, TJ
    TUMEY, ML
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) : 7844 - 7846
  • [9] SOLID-STATE CHEMISTRY - DISCRETE TRIMETHYLSILYLMETHYLENE
    CHEDEKEL, MR
    SKOGLUND, M
    KREEGER, RL
    SHECHTER, H
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) : 7846 - 7848
  • [10] PARA-TOLUENESULFONYLDIAZOACETATES - REAGENTS FOR PHOTOAFFINITY LABELING
    CHOWDHRY, V
    WESTHEIMER, FH
    [J]. BIOORGANIC CHEMISTRY, 1978, 7 (02) : 189 - 205