FACILE SYNTHESES OF GEM-DIFLUOROALKENES FROM CHLORODIFLUOROMETHYLKETONES

被引:9
作者
BEGUE, JP
BONNETDELPON, D
PERCY, JM
ROCK, MH
WILKES, RD
机构
[1] UNIV BIRMINGHAM,SCH CHEM,BIRMINGHAM B15 2TT,W MIDLANDS,ENGLAND
[2] FAC PHARM CHATENAY MALABRY,BIOCIS,CNRS,F-92296 CHATENAY MALABRY,FRANCE
关键词
D O I
10.1039/c39950001857
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chlorodifluoromethyl ketones reacted with diazomethane to afford epoxides in high yield; upon treatment with butyllithium, the epoxides underwent efficient ring opening to afford 3,3-difluoro-2-alkyl-alken-1-ols, suitable substrates for sigmatropic rearrangement leading to compounds containing a CF2 group in mid-chain.
引用
收藏
页码:1857 / 1857
页数:1
相关论文
共 17 条
  • [1] SYNTHESIS OF 3-GEM-DIFLUORO-2-ETHOXY ALLYLIC ALCOHOLS FROM ETHYL CHLORODIFLUOROACETATE
    BEGUE, JP
    BONNETDELPON, D
    ROCK, MH
    [J]. TETRAHEDRON LETTERS, 1994, 35 (33) : 6097 - 6100
  • [2] THE WITTIG REACTION OF PERFLUORO-ACID DERIVATIVES - ACCESS TO FLUORINATED ENOL ETHERS, ENAMINES, AND KETONES
    BEGUE, JP
    BONNETDELPON, D
    MESUREUR, D
    NEE, G
    WU, SW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) : 3807 - 3814
  • [3] BENNETT AJ, 1992, SYNLETT, P483
  • [4] NEW FLUORINATED CHIRAL SYNTHONS
    BRAVO, P
    FARINA, A
    FRIGERIO, M
    MEILLE, SV
    VIANI, F
    SOLOSHONOK, V
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (06) : 987 - 1004
  • [5] CONVENIENT PROCEDURES FOR CONVERSION OF CARBONYL-COMPOUNDS TO GEM-DIFLUOROOLEFINS AND THEIR SELECTIVE REDUCTIONS TO MONOFLUOROOLEFINS
    HAYASHI, S
    NAKAI, T
    ISHIKAWA, N
    BURTON, DJ
    NAAE, DG
    KESLING, HS
    [J]. CHEMISTRY LETTERS, 1979, (08) : 983 - 986
  • [6] HERON TF, 1994, TETRAHEDRON-ASYMMETR, V5, P2269
  • [7] A NOVEL SYNTHESIS OF 1,1-DIFLUOROOLEFINS FROM 1,1,1-TRIFLUOROETHYL P-TOLUENESULFONATE VIA BORON ATE-COMPLEX
    ICHIKAWA, J
    SONODA, T
    KOBAYASHI, H
    [J]. TETRAHEDRON LETTERS, 1989, 30 (13) : 1641 - 1644
  • [8] ORGANOCUPRATE-INDUCED SUBSTITUTION OF THE ENOL OXYGEN MOIETY IN 2,2-DIFLUORO ENOL PHOSPHATES WITH ALLYL HALIDES - A NOVEL ROUTE TO GEM-DIFLUOROOLEFINS FROM CHLORODIFLUOROMETHYL KETONES
    ISHIHARA, T
    YAMANA, M
    ANDO, T
    [J]. TETRAHEDRON LETTERS, 1983, 24 (50) : 5657 - 5660
  • [9] REACTIONS OF 2,2,2-TRIFLUOROETHOXYTYIOBENZENE AND 2,2,2-TRIFLUOROETHYLTHIOBENZENE WITH LITHIUM DIALKYLAMIDES - FORMATION OF PHENYLTHIOYNAMINES
    NAKAI, T
    TANAKA, K
    ISHIKAWA, N
    [J]. CHEMISTRY LETTERS, 1976, (11) : 1263 - 1266
  • [10] SYNTHESIS AND INHIBITORY ACTIVITY OF DIFLUOROKETONE SUBSTRATE-ANALOGS OF N-MYRISTOYLTRANSFERASE
    NEDER, KM
    FRENCH, SA
    MILLER, SPF
    [J]. TETRAHEDRON, 1994, 50 (33) : 9847 - 9864