SYNTHESIS OF SUBSTITUTED CYCLOPROPANES FROM 1,3-DIOLS THROUGH THE CORRESPONDING CYCLIC SULFATES

被引:16
作者
GUIJARRO, D [1 ]
YUS, M [1 ]
机构
[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALACANT,SPAIN
关键词
D O I
10.1016/0040-4020(95)00708-G
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of different cyclic sulfates 2 (easily prepared from the corresponding 1,3-diols 1 following the Sharpless methodology) with an excess of lithium powder and a catalytic amount of DTBB (5 mol%) leads to the corresponding substituted cyclopropanes 3 through a gamma-elimination process, the sulfate ion acting as leaving group.
引用
收藏
页码:11445 / 11456
页数:12
相关论文
共 31 条
  • [1] ALEKSYUK MP, 1971, T VORONEZH TEKHNOL I, V19, P27
  • [2] ARAI K, 1989, CHEM PHARM BULL, V37, P3117
  • [3] BAO W, 1994, HECHENG HUAXUE, V2, P33
  • [4] BAUMSTARK AL, 1977, TETRAHEDRON LETT, P3003
  • [5] BEELS CMD, 1990, SYNLETT, P479
  • [6] LANTHANIDES IN ORGANIC-SYNTHESIS - EU+3-CATALYZED MICHAEL ADDITION OF 1,3-DICARBONYL COMPOUNDS
    BONADIES, F
    LATTANZI, A
    ORELLI, LR
    PESCI, S
    SCETTRI, A
    [J]. TETRAHEDRON LETTERS, 1993, 34 (47) : 7649 - 7650
  • [7] 1,5-INTRAMOLECULAR VS 1,6-INTRAMOLECULAR HOMOLYTIC AROMATIC-SUBSTITUTION BY VINYL RADICALS
    CITTERIO, A
    SEBASTIANO, R
    MARONATI, A
    SANTI, R
    BERGAMINI, F
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (13) : 1517 - 1518
  • [8] CLARK T, 1979, COMPREHENSIVE ORGANI, P96
  • [9] SYNTHESIS OF SUBSTITUTED 14-CROWN-4 COMPOUNDS
    CZECH, BP
    ZAZULAK, W
    KUMAR, A
    OLSHER, U
    FEINBERG, H
    COHEN, S
    SHOHAM, G
    DALLEY, NK
    BARTSCH, RA
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (06) : 1389 - 1400
  • [10] DAVIES HM, 1991, COMPREHENSIVE ORGANI