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

页码：586 / 593

页数：8

共 43 条

[41] 1,3-Dipolar Cycloadditions of Nitrones to Hetero-substituted Alkenes Part 2: Sila-, Thia-, Phospha- and Halo-substituted Alkenes [J].

Thanh Binh Nguyen ;

Martel, Arnaud ;

Gaulon-Nourry, Catherine ;

Dhal, Robert ;

Dujardin, Gilles .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2012, 44 (01) :1-81

[42] The IEF version of the PCM solvation method:: an overview of a new method addressed to study molecular solutes at the QM ab initio level [J].

Tomasi, J ;

Mennucci, B ;

Cancès, E .

JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 1999, 464 (1-3) :211-226

[43] Synthesis of 5-trichloromethyl-Δ4-1,2,4-oxadiazolines and their rearrangement into formamidine derivatives [J].

Wagner, Gabriele ;

Garland, Tim .

TETRAHEDRON LETTERS, 2008, 49 (22) :3596-3599

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