Synthesis and Epoxidation of 5-(2-Aminoethyl)bicyclo[2.2.1]hept-2-ene Derivatives

被引：0
|
作者：
L. I. Kas'yan
I. N. Tarabara
A. O. Kas'yan
机构：
[1] Dnepropetrovsk State University,
[2] Ukrainian State University of Chemical Technology,undefined
来源：
Russian Journal of Organic Chemistry | 2002年 / 38卷
关键词：
Anhydride; Epoxidation; Isocyanate; Benzoyl; Carboxamides;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A number of derivatives of 5-(2-aminoethyl)bicyclo[2.2.1]hept-2-ene (85-90% of the endo isomer) were synthesized by reactions with p-nitrobenzenesulfonyl chloride, p-toluenesulfonyl chloride, benzoyl chloride, p-nitrobenzoyl chloride, benzyl isocyanate, m-tolyl isocyanate, phenyl isothiocyanate, and endic anhydride. By reactions of the resulting sulfon- and carboxamides with peroxyphthalic acid generated in situ from phthalic anhydride and 40-45% hydrogen peroxide the corresponding epoxy derivatives were obtained. These reactions were not accompanied by heterocyclization into azabrendane derivatives, which is typical of homologous N-(p-nitrophenylsulfonyl)-endo-5-aminomethylbicyclo[2.2.1]hept-2-ene.
引用
收藏
页码：19 / 25
页数：6
相关论文
共 50 条
  • [31] ANHARMONIC SKELETAL DEFORMATION IN BICYCLO[2.2.1]HEPT-2-ENE AND 7-OXABICYCLO[2.2.1]HEPTANE
    CARLILE, RP
    SMITHSON, TL
    WEISER, H
    JOURNAL OF MOLECULAR STRUCTURE, 1983, 96 (3-4) : 283 - 291
  • [32] W(II)-catalyzed hydroarylation of bicyclo[2.2.1]-hept-2-ene by simple arenes
    Malinowska, A
    Czelusniak, I
    Górski, M
    Szymanska-Buzar, T
    TETRAHEDRON LETTERS, 2005, 46 (09) : 1427 - 1431
  • [33] RADICAL HOMOPOLYMERIZATION OF 5-CYANOBICYCLO [2.2.1]-HEPT-2-ENE
    IMOTO, M
    ITO, T
    OTSU, T
    JOURNAL OF POLYMER SCIENCE PART B-POLYMER LETTERS, 1963, 1 (06): : 295 - &
  • [34] Rearrangement of a bicyclo[3.2.0]hept-2-ene to a bicyclo[4.1.0]hept-4-ene
    Behrendt, U
    Gabor, B
    Mynott, R
    Butenschon, H
    LIEBIGS ANNALEN, 1996, (07): : 1167 - 1173
  • [35] CALCIUM-OXIDE AS A CATALYST FOR THE ISOMERIZATION OF 5-VINYLBICYCLO[2.2.1]HEPT-2-ENE TO 5-ETHYLIDENEBICYCLO[2.2.1]HEPT-2-ENE IN THE LIQUID-PHASE
    BABA, T
    ENDOU, T
    HANDA, H
    ONO, Y
    APPLIED CATALYSIS A-GENERAL, 1993, 97 (01) : L19 - L23
  • [36] Modern Valence Bond Description of the Electronic Mechanism of a [1,3] Sigmatropic Rearrangement Linking Bicyclo[3.2.0]hept-2-ene and Bicyclo[2.2.1]hept-2-ene (Norbornene)
    Karadakov, Peter B.
    Cooper, David L.
    Uhe, Andreas
    INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2009, 109 (09) : 1807 - 1811
  • [37] THERMAL REARRANGEMENT OF 5-METHYLENEBICYCLO[2.2.1]HEPT-2-ENE
    MATTESON, DS
    DRYSDALE, JJ
    SHARKEY, WH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (11) : 2853 - 2857
  • [38] A novel catalytic route to 2-bicyclo[2.2.1]hept-2-ylidenebicyclo[2.2.1]-heptane involving C-H bond activation of bicyclo [2.2.1]hept-2-ene
    Malinowska, A
    Czelusniak, I
    Górski, M
    Szymanska-Buzar, T
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 226 (02) : 259 - 262
  • [39] PROBING THE ROTATIONAL DISORDER OF MOLECULES IN PLASTIC BICYCLO[2.2.1]HEPT-2-ENE WITH IMPLANTED MUONS
    RICCO, M
    DERENZI, R
    RODUNER, E
    PHYSICS LETTERS A, 1988, 129 (07) : 390 - 394
  • [40] Alternating ring-opening metathesis copolymerization of bicyclo[2.2.1]hept-2-ene and cyclopentene
    AlSamak, B
    Carvill, AG
    Hamilton, JG
    Rooney, JJ
    Thompson, JM
    CHEMICAL COMMUNICATIONS, 1997, (21) : 2057 - 2058
12345