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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 21期

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

页码：6393 / 6398

页数：6

共 24 条

[11] 2-DIAZO-3,3,3-TRIFLUOROPROPIONYL CHLORIDE - REAGENT FOR PHOTOAFFINITY LABELING
CHOWDHRY, V
VAUGHAN, R
WESTHEIMER, FH
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1976, 73 (05) : 1406 - 1408
[12] PARA-TOLUENESULFONYLDIAZOACETATES AS PHOTOAFFINITY LABELING REAGENTS
CHOWDHRY, V
WESTHEIMER, FH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) : 309 - 310
[13] CHOWDHRY V, 1977, THESIS HARVARD U
[14] Eaborn C., 1968, ORGANOMETALLIC COM 1, V1
[15] FRIEDMAN L, 1970, CARBONIUM IONS, V2, pCH6
[16] SILICON-CARBON MULTIPLE-BONDED (PI-PI) INTERMEDIATES - 1ST GENERATION AND REACTIONS OF SILAETHENE [H2SI=CH2] AND SILANONE [H2SI=O]
GOLINO, CM
BUSH, RD
SOMMER, LH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (25) : 7371 - 7372
[17] UNSTABLE SILICON ANALOGS OF UNSATURATED-COMPOUNDS
GUSELNIKOV, LE
NAMETKIN, NS
VDOVIN, VM
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1975, 8 (01) : 18 - 25
[18] GAS-PHASE CARBENE REACTIONS
JONES, M
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (12) : 415 - 421
[19] KIRMSE W, 1967, TETRAHEDRON LETT, P1833
[20] KIRMSE W, 1973, CARBENE CHEM

← 1 2 3 →