Regio- and stereoselectivity of polar [2+3] cycloaddition reactions between (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone and selected (E)-2-substituted nitroethenes

被引:63
作者
Jasinski, Radomir [1 ]
Ziolkowska, Magda [2 ]
Demchuk, Oleh M. [3 ]
Maziarka, Agata [1 ]
机构
[1] Cracow Univ Technol, Inst Organ Chem & Technol, PL-31155 Krakow, Poland
[2] AGH Univ Sci & Technol, Fac Energy & Fuels, PL-30059 Krakow, Poland
[3] Marie Curie Sklodowska Univ, Dept Organ Chem, PL-20614 Lublin, Poland
来源
CENTRAL EUROPEAN JOURNAL OF CHEMISTRY | 2014年 / 12卷 / 05期
关键词
2+3] cycloaddition; Nitrone; Nitroalkene; Regioselectivity; Stereoselectivity; (Z)-C; N-DIPHENYLNITRONE; NITRO; DFT;
D O I
10.2478/s11532-014-0518-2
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
[2+3] Cycloaddition reactions of the highly reactive (Z)-C-(3,4,5-trimethoxyphenyl)-N-methylnitrone with (E)-2-R-nitroethenes proceed under mild conditions and yield mixtures of stereoisomeric 2-methyl-3-(3,4,5-trimethoxyphenyl)-4-nitro-5-R-isoxazolidines. The effect of regiospecificity of the cycloadditions may be accounted for by the theory of electrophilicity indexes. Stereoselectivity, however, is determined by a compilation of steric and secondary orbital effects.
引用
收藏
页码:586 / 593
页数:8
相关论文
共 43 条
[1]  
Agrawal J. P., 2007, CHEM EXPLOSIVES
[2]  
[Anonymous], 2000, Structure Determination of organic compounds
[3]  
[Anonymous], 1984, 1 3 DIPOLAR CYCLOADD
[4]   Recent synthetic developments in the nitro to carbonyl conversion (Nef reaction) [J].
Ballini, R ;
Petrini, M .
TETRAHEDRON, 2004, 60 (05) :1017-1047
[5]  
Baranski, 2002, WIAD CHEM, V56, P829
[6]  
BARANSKI A, 1990, CHEM HETEROCYCL COMP, V26, P371
[7]  
Baranski A., 2011, POSTEPY INZYNIERII T
[8]   CONJUGATED NITROALKENES - VERSATILE INTERMEDIATES IN ORGANIC-SYNTHESIS [J].
BARRETT, AGM ;
GRABOSKI, GG .
CHEMICAL REVIEWS, 1986, 86 (05) :751-762
[9]  
Belen'kii LI, 2008, NITRILE OXIDES, NITRONES, AND NITRONATES IN ORGANIC SYNTHESIS: NOVEL STRATEGIES IN SYNTHESIS, 2ND EDITION, P1
[10]   1,1,1-TRICHLORO-2-ARYLAMINO-3-NITROPROPANES [J].
BROWER, F ;
BURKETT, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (05) :1082-1084