DIMETHYLDIOXIRANE OXIDATION OF ENAMINES - 1ST SPECTRAL EVIDENCE FOR ENAMINE OXIDES BY STABILIZATION THROUGH N-SILYLATION

被引：27
作者：
ADAM, W
AHRWEILER, M
PAULINI, K
REISSIG, HU
VOERCKEL, V
机构：
[1] TH MERSEBURG,INST TECH CHEM,O-4200 MERSEBURG,GERMANY
[2] UNIV WURZBURG,INST ORGAN CHEM,W-8700 WURZBURG,GERMANY
[3] TH DARMSTADT,INST ANORGAN CHEM,W-6100 DARMSTADT,GERMANY
来源：
CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 12期
关键词：
EPOXIDATION; ENAMINES; N-SILYLATED; INDOLES; EPOXIDES; DISILYLAMINOXIDES; KETONES ALPHA-AMINO; INDOLINONES; DIMETHYLDIOXIRANE;
D O I：
10.1002/cber.19921251217
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The oxygen transfer to the enamines 1a - f by dimethyldioxirane (DMD) in acetone solution leads to the alpha-amino epoxides 2a - f. The stability of the alpha-amino epoxides 2a - f depends only on the type of substitution at the nitrogen atom. Thus, while the epoxides 2a, b could be characterized spetroscopically, the epoxidation of the enamines 1c - f resulted in the corresponding alpha-amino ketone 3c (hydride shift) and the amides 4d - f (alkyl shift). The alpha-[bis(trimethylsilyl)]amino epoxides 2a, b represent the first observable enamine oxides and emphasize the value of stabilizing such labile epoxides through disilylation of the enamine nitrogen atom.
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页码：2719 / 2721
页数：3
相关论文
共 15 条
  • [1] EPOXIDATION OF ENAMINES BY DIMETHYLDIOXIRANE - FORMATION OF 1,4-DIOXANES BY ENAMINE EPOXIDE DIMERIZATION
    ADAM, W
    PETERS, EM
    PETERS, K
    VONSCHNERING, HG
    VOERCKEL, V
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1992, 125 (05): : 1263 - 1266
  • [2] A CONVENIENT PREPARATION OF ACETONE SOLUTIONS OF DIMETHYLDIOXIRANE
    ADAM, W
    BIALAS, J
    HADJIARAPOGLOU, L
    [J]. CHEMISCHE BERICHTE, 1991, 124 (10) : 2377 - 2377
  • [3] STUDIES ON THE OXIDATION OF ENAMINES WITH MOLECULAR-OXYGEN .3. OXIDATION OF SOME AMINO STYRENES
    BLAU, K
    BURGEMEISTER, I
    GRASNICK, J
    VOERCKEL, V
    [J]. JOURNAL FUR PRAKTISCHE CHEMIE, 1991, 333 (03): : 455 - 466
  • [4] STUDIES ON THE OXIDATION OF ENAMINES WITH MOLECULAR-OXYGEN .2. OXIDATION OF 1-AMINO BUT-1-ENES
    BLAU, K
    KAPST, U
    VOERCKEL, V
    [J]. JOURNAL FUR PRAKTISCHE CHEMIE, 1989, 331 (04): : 671 - 676
  • [5] OXIDATION OF SOME PIPERIDINO ALKENES
    BLAU, K
    VOERCKEL, V
    [J]. JOURNAL FUR PRAKTISCHE CHEMIE, 1989, 331 (02): : 285 - 292
  • [6] Borsche W, 1941, LIEBIGS ANN CHEM, V549, P238
  • [7] IMPROVED TITANIUM TETRACHLORIDE PROCEDURE FOR ENAMINE SYNTHESIS .2. SCOPE OF THE REACTION
    CARLSON, R
    NILSSON, A
    [J]. ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (01): : 49 - 53
  • [8] INDOLENINE OXIDES .7. PHOTODECARBONYLATION OF 2 3,3-DIMETHYL-2-INDOLINONES
    DOPP, D
    WEILER, H
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1979, 112 (12): : 3950 - 3954
  • [9] PAULINI K, 1991, LIEBIGS ANN CHEM, P455
  • [10] PAULINI K, UNPUB
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