Regiospecific formation of the nitromethyl-substituted 3-phenyl-4,5-dihydroisoxazole via [3 + 2] cycloaddition.

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Monatshefte Fur Chemie Pub Date : 2018-01-01 Epub Date: 2018-08-20 DOI:10.1007/s00706-018-2227-6

Barbara Mirosław, Dmytro Babyuk, Agnieszka Łapczuk-Krygier, Agnieszka Kącka-Zych, Oleg M Demchuk, Radomir Jasiński

引用次数: 19

Abstract

Abstract: 5-(Nitromethyl)-3-phenyl-4,5-dihydroisoxazole was obtained as a product of a high-yielding [3 + 2] cycloaddition reaction of in situ-generated benzonitrile N-oxide and 3-nitroprop-1-ene. For the first time, the regiochemistry of this reaction was unambiguously proven by X-ray structural analysis. The quantum-chemical calculation performed at the M06-2X/6-31G(d) (PCM) theoretical level affords a basis for explaining the course of reaction as well as the nature of transition states. Next, further DFT calculations together with spectral data shed light on structural aspects of the product.

Graphical abstract:

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硝基甲基取代的3-苯基-4,5-二氢异恶唑的区域特异性形成 + 2] 环加成。

摘要：5-（硝基甲基）-3-苯基-4,5-二氢异恶唑是一种高产[3 + 2] 原位生成的苄腈N-氧化物和3-硝基丙-1-烯的环加成反应。X射线结构分析首次明确证明了该反应的区域化学性质。在M06-2X/6-31G（d）（PCM）理论水平上进行的量子化学计算为解释反应过程以及过渡态的性质提供了基础。接下来，进一步的DFT计算以及光谱数据揭示了产品的结构方面。图形摘要：

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Monatshefte Fur Chemie 化学-化学综合

CiteScore

3.70

自引率

5.60%

发文量

116

审稿时长

3.3 months

期刊介绍： "Monatshefte für Chemie/Chemical Monthly" was originally conceived as an Austrian journal of chemistry. It has evolved into an international journal covering all branches of chemistry. Featuring the most recent advances in research in analytical chemistry, biochemistry, inorganic, medicinal, organic, physical, structural, and theoretical chemistry, Chemical Monthly publishes refereed original papers and a section entitled "Short Communications". Reviews, symposia in print, and issues devoted to special fields will also be considered.