ALPHA-METHOXYLATION OF UNSATURATED CARBONYL-COMPOUNDS

被引:8
|
作者
FEUERER, A [1 ]
SEVERIN, T [1 ]
机构
[1] UNIV MUNICH,INST PHARM & LEBENSMITTELCHEM,D-80333 MUNICH,GERMANY
来源
JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 20期
关键词
D O I
10.1021/jo00099a037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
alpha-Methoxylation of enals or enones can be performed in high yield by a simple one-pot reaction sequence: Bromination of unsaturated hydrazones, HBr-elimination, and addition of methanol leads to the formation of beta-bromo-alpha-methoxy hydrazones (11), which after hydrolysis and HBr-elimination yields the alpha-methoxy enals or alpha-methoxy enones (13), respectively.
引用
收藏
页码:6026 / 6029
页数:4
相关论文
共 50 条
  • [1] ELECTROPHILIC BETA-BROMINATION AND NUCLEOPHILIC ALPHA-METHOXYLATION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
    FISCHER, H
    KLIPPE, M
    LERCHE, H
    SEVERIN, T
    WANNINGER, G
    CHEMISCHE BERICHTE, 1990, 123 (02) : 399 - 404
  • [2] REGIOSPECIFIC SYNTHETIC ROUTES TO ALPHA-SELENO CARBONYL-COMPOUNDS AND TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
    DENIS, JN
    DUMONT, W
    KRIEF, A
    TETRAHEDRON LETTERS, 1976, (06) : 453 - 456
  • [3] MODE OF ACTION OF ALPHA,BETA UNSATURATED CARBONYL-COMPOUNDS
    LARSEN, J
    OLSON, LW
    JOURNAL OF PHYTOPATHOLOGY-PHYTOPATHOLOGISCHE ZEITSCHRIFT, 1992, 135 (01): : 1 - 5
  • [4] REACTIONS OF BENZYNE WITH ALPHA,BETA UNSATURATED CARBONYL-COMPOUNDS
    BOWNE, AT
    LEVIN, RH
    TETRAHEDRON LETTERS, 1974, (23) : 2043 - 2046
  • [5] REACTION OF ANTHRAHYDROQUINONES WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
    KROHN, K
    MIEHE, F
    LIEBIGS ANNALEN DER CHEMIE, 1985, (07): : 1329 - 1335
  • [6] EPOXIDATION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS BY DIMETHYLDIOXIRANE
    BAUMSTARK, AL
    HARDEN, DB
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26): : 7615 - 7618
  • [7] ASYMMETRIC HYDROSILYLATION OF ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
    HAYASHI, T
    YAMAMOTO, K
    KUMADA, M
    TETRAHEDRON LETTERS, 1975, (01) : 3 - 6
  • [8] REACTION OF CARBONYLNITROSOMETHANE WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
    ENSLEY, HE
    BRAUSCH, JF
    UGARKAR, BG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1987, 194 : 290 - ORGN
  • [9] CONDENSATION OF HEXAFLUOROACETONE WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
    FOKIN, AV
    KOLOMIETS, AF
    KROLEVETS, AA
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1978, 27 (04): : 849 - 849
  • [10] HETERODIENE SYNTHESES WITH ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS
    DESIMONI, G
    TACCONI, G
    CHEMICAL REVIEWS, 1975, 75 (06) : 651 - 692