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

中文翻译：

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

摘要

5-(硝基甲基)-3-苯基-4,5-二氢异恶唑是原位生成的苯甲腈N-氧化物与3-硝基丙烯-1-烯进行高产率[3 + 2]环加成反应的产物。该反应的区域化学首次通过 X 射线结构分析得到明确证明。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 计算和光谱数据揭示了产品的结构方面。

图形概要