PRESSURE-INDUCED DIASTEREOSELECTIVITY IN PHOTOCHEMICAL [2 + 2] CYCLOADDITION REACTIONS

被引:13
作者
BUBACK, M [1 ]
BUNGER, J [1 ]
TIETZE, LF [1 ]
机构
[1] UNIV GOTTINGEN,INST ORGAN CHEM,W-3400 GOTTINGEN,GERMANY
来源
CHEMISCHE BERICHTE-RECUEIL | 1992年 / 125卷 / 11期
关键词
HIGH-PRESSURE REACTIONS; 2 + 2] PHOTOCYCLOADDITION REACTIONS; DIASTEREOSELECTIVITY; CYCLOPENTENONES; CYCLOPENTENES;
D O I
10.1002/cber.19921251132
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Photochemical [2 + 2] cycloaddition reactions under high pressure of cyclopentenone 1 a or cyclohexenone 15, as well as of 1 a or 3-substituted cyclopentenones 1 b - d with cyclopentene (2), and of 1b with 3,3-dimethyl-1-butene (18) are described. Whereas the pressure dependence on the regioselectivity in the photoaddition of 1 a and 15 is very small, DELTADELTAV * values up to 2.0 +/- 0.3 cm3 . mol-1 have been found for the diastereoselectivity in the reactions of 1 a - d with 2 and of 1 b with 18.
引用
收藏
页码:2577 / 2582
页数:6
相关论文
共 34 条
  • [1] ACTIVATION AND REACTION VOLUMES IN SOLUTION
    ASANO, T
    LENOBLE, J
    [J]. CHEMICAL REVIEWS, 1978, 78 (04) : 407 - 489
  • [2] BECKER HGO, 1983, EINFUHRUNG PHOTOCHEM, P346
  • [3] BIPHASIC PHOTOCHEMISTRY - MICELLE SOLUTIONS AS MEDIA FOR PHOTOCHEMICAL CYCLO-ADDITIONS OF ENONES
    BERENJIAN, N
    DEMAYO, P
    STURGEON, ME
    SYDNES, LK
    WEEDON, AC
    [J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (04): : 425 - 436
  • [4] INTERMOLECULAR AND INTRAMOLECULAR HETERO DIELS-ALDER REACTIONS .22. HETERO DIELS-ALDER REACTIONS OF ENAMINE CARBALDEHYDES AT HIGH-PRESSURE STUDIED BY ONLINE IR DETECTION
    BUBACK, M
    TOST, W
    TIETZE, LF
    VOSS, E
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (04): : 781 - 785
  • [5] INTERMOLECULAR AND INTRAMOLECULAR HETERO DIELS-ALDER REACTIONS .26. DIASTEREOSELECTIVITY AND KINETICS OF INTERMOLECULAR HETERO DIELS-ALDER REACTIONS UNDER HIGH-PRESSURE - A SIGNIFICANT PRESSURE-INDUCED INCREASE IN STEREOSELECTIVITY
    BUBACK, M
    TOST, W
    HUBSCH, T
    VOSS, E
    TIETZE, LF
    [J]. CHEMISCHE BERICHTE, 1989, 122 (06) : 1179 - 1186
  • [6] BUCHI G, 1973, J AM CHEM SOC, V95, P540
  • [7] Buchi G., 1970, J AM CHEM SOC, V92, P2165
  • [8] THE ISOINVERSION PRINCIPLE - A GENERAL-MODEL OF CHEMICAL SELECTIVITY
    BUSCHMANN, H
    SCHARF, HD
    HOFFMANN, N
    ESSER, P
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1991, 30 (05) : 477 - 515
  • [9] Buschmann H., 1991, ANGEW CHEM, V103, P480
  • [10] PHOTOCHEMICAL CYCLOADDITION . SOME APPLICATIONS OF USE OF ENOLIZED BETA-DIKETONES
    CHALLAND, BD
    HIKANO, H
    KORNIS, G
    LANGE, G
    DEMAYO, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (04) : 794 - &