Investigation into the regiochemistry of some isoxazoles derived from 1,3-dipolar cycloaddition of 4-nitrobenzonitrile oxide with some dipolarophiles: A combined theoretical and experimental studies

被引：8
|
作者：
Dorostkar-Ahmadi, N. [1 ]
Bakavoli, M. [1 ]
Moeinpour, F. [2 ]
Davoodnia, A. [1 ]
机构：
[1] Islamic Azad Univ, Fac Sci, Dept Chem, Mashhad Branch, Mashhad, Iran
[2] Islamic Azad Univ, Fac Sci, Dept Chem, Bandar Abbas Branch, Bandar Abbas, Iran
来源：
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY | 2011年 / 79卷 / 05期
关键词：
Regioselectivity; 1,3-dipolar cycloaddition; Nitrile oxide; DFT-based reactivity indexes; B3LYP calculations; QUANTITATIVE CHARACTERIZATION; REGIOSELECTIVITY; ELECTROPHILICITY; NITRILIMINE; REACTIVITY;
D O I：
10.1016/j.saa.2011.04.071
中图分类号：
O433 [光谱学];
学科分类号：
0703 ; 070302 ;
摘要：
Reaction of 4-nitrobenzonitrile oxide(2) which was generated in situ with acrylo nitrile (3), methyl methacrylate (4) and allyl bromide (5) as dipolarphile afforded the new 7a, 8a and 9a compounds respectively. Reactivity and regiochemistry of these reactions were investigated using activation energy calculations and density functional theory (DFT)-based reactivity indexes. The theoretical (CNMR)-C-13 chemical shifts of the cycloadducts which were obtained by CIAO method were comparable with the observed values. (C) 2011 Elsevier B.V. All rights reserved.
引用
收藏
页码：1375 / 1380
页数：6
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