分子内1,3-偶极环加成反应研究(Ⅴ)——N-4-戊烯基硝酮体系环加成区域选择性产物的色谱分析及结构鉴定

STUDIES ON INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION REACTIONS (Ⅴ)——CHROMATOGRAPHIC ANALYSIS AND STRUCTURAL DETERMINATION FOR REGIOSELECTIVE PRODUCTS OF 4-PENTENYLNITRONES CYCLOADDITION

利用色谱法、气-质联用技术及碳-13核磁共振,定量地研究了N-4-戊烯基硝酮体系区域选择性产物的结构和含量.实验结果表明气相色谱法是对N-4-戊烯基硝酮环加成产物分析的有效方法.所得结果与1,3-偶极环加成反应的动力学控制、硝酮偶极体系的LUMO轨道控制及过渡态理论相符,它为分子轨道理论在有机合成中的应用研究提供了重要的实验依据.

The structures and contents of the regioselective products of N-4-pentenyl nitrone Ⅱ and Ⅲ are investigated quantitatively via chroma- tographic methods(GC, LC), combined GC-Mass spectrometry and ^(13)CNMR specctroscopy. The experiments indicate the GC chromatography is a effe- ctive method for the analysis of cycloaddition products of N-4-pentenylni- trones and agree well with dynamic control of the cycloaddition, the LUMO control of the nitrone dipolar system and the transition theory. They pro- vide important experimental basis for molecular orbital theory and organic synthesis studies.