Isomerization of 3-unsubstituted 4,5-dihydroisoxazoles over alumina. A new synthesis of β-hydroxy nitriles

被引：1
作者：
Mochalov, S. S. [1 ]
Fedotov, A. N. [1 ]
Trofimova, E. V. [1 ]
Gazzaeva, R. A. [2 ]
Zefirov, N. S. [1 ]
机构：
[1] Moscow MV Lomonosov State Univ, Fac Chem, Leninskie Gory 1, Moscow 119991, Russia
[2] Khetagurov North Ossetian State Univ, Ul Vatutina 44-46, Vladikavkaz 362025, Russia
来源：
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 52卷 / 03期
关键词：
NITROSYL CHLORIDE; FULMINIC ACID; ABSOLUTE-CONFIGURATION; ARYLCYCLOPROPANES; DERIVATIVES; OXIDE; 3-BROMO-2-ISOXAZOLINES; CYANOHYDROXYLATION; CYCLOADDITIONS; 2-ISOXAZOLINES;
D O I：
10.1134/S1070428016030179
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
3-Unsubstituted 4,5-dihydroisoxazoles obtained by nitrosation of arylcyclopropanes are capable of undergoing efficient isomerization into 3-aryl-3-hydroxypropanenitriles during chromatography on alumina.
引用
收藏
页码：397 / 403
页数：7
相关论文
共 40 条
  • [1] Akhrem A. A., 1981, CHEM HETEROCYCL COMP, V17, P853, DOI [10.1007/BF00505584, DOI 10.1007/BF00505584]
  • [2] 2-isoxazolines from arylcyclopropanes: I. Monoarylcyclopropanes in a reaction with nitrosyl chloride activated by sulfur(IV) oxide
    Bondarenko, OB
    Gavrilova, AY
    Kazantseva, MA
    Tikhanushkina, VN
    Nifant'ev, EE
    Saginova, LG
    Zyk, NV
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (02) : 249 - 255
  • [3] 4,5-dihydroisoxazoles from arylcyclopropanes by reactions with nitrosyl chloride activated with sulfur trioxide
    Bondarenko, OB
    Gavrilova, AY
    Saginova, LG
    Zyk, NV
    Zefirov, NS
    [J]. RUSSIAN CHEMICAL BULLETIN, 2003, 52 (03) : 778 - 778
  • [4] Synthesis of 4,5-dihydroisoxazoles from arylcyclopropanes and nitrosyl chloride
    Bondarenko, OB
    Gavrilova, AY
    Saginova, LG
    Zyk, NV
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 39 (07) : 1021 - 1024
  • [5] BRANDI A, 1982, SYNTHESIS-STUTTGART, P719
  • [6] SIMPLE INSITU PREPARATION OF FULMINIC ACID
    DESARLO, F
    BRANDI, A
    GUARNA, A
    GOTI, A
    COREZZI, S
    [J]. TETRAHEDRON LETTERS, 1983, 24 (17) : 1815 - 1816
  • [7] THE CHEMISTRY OF FULMINIC ACID REVISED
    DESARLO, F
    GUARNA, A
    BRANDI, A
    GOTI, A
    [J]. TETRAHEDRON, 1985, 41 (22) : 5181 - 5185
  • [8] First total synthesis of (±)-AM6898A and (±)-AM6898D
    Fukuda, Y
    Okamoto, Y
    [J]. TETRAHEDRON, 2002, 58 (13) : 2513 - 2521
  • [9] Enantiomerically pure isoxazolines by stereoselective 1,3-dipolar cycloaddition of silyl nitronates
    Galley, G
    Jones, PG
    Patzel, M
    [J]. TETRAHEDRON-ASYMMETRY, 1996, 7 (07) : 2073 - 2082
  • [10] Gazzaeva R A, 1984, CHEM HETEROCYCL COMP, V20, P246, DOI [10.1007/BF00515629, DOI 10.1007/BF00515629]
1234