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对称双吡咯甲烷的合成与分子内氢键的研究
引用本文:陈清奇,金声.对称双吡咯甲烷的合成与分子内氢键的研究[J].高等学校化学学报,1995,16(5):725-729.
作者姓名:陈清奇  金声
作者单位:中国科学院感光化学研究所,北京大学化学系
摘    要:5-甲基吡咯-2-羧酸酯在磺酰氢,溴或四乙酸铅作用下,生成相应的在5-甲基上含取代基的产物,后者不经分离不便可自缩合得标题化合物,核磁共振氢谱研究和分子构象木匠,当3,3位的取代基为甲酸(酯)基或乙酸(酯)基时,可形成3,3位酯基与另一吡咯环上的氮氢之间的分子内氢键,而3,3位是其它取代基,如乙酰基,丙酸(酯)基,丁酸(酯)基时不能形成类似的分子内氢键。

关 键 词:双吡咯甲烷  氢键  NMR  合成

Synthesis and Intramolecular Hydrogen Bonding ofSymmetric Dipyrrylmethanes
CHEN Qing-Qi, WANG Chang-Qi,CHENG Ling-Jiang, MA Jin-Shi.Synthesis and Intramolecular Hydrogen Bonding ofSymmetric Dipyrrylmethanes[J].Chemical Research In Chinese Universities,1995,16(5):725-729.
Authors:CHEN Qing-Qi  WANG Chang-Qi  CHENG Ling-Jiang  MA Jin-Shi
Abstract:The title compounds were prepared by converting ethyl 5-methylpyrrole-2-car boxylates into corresponding 5-methyl substituted pyrroles oxydized by surfuryl chloride,bromine,or lead tetraacetate, and then self-condensed without separation and purification.The 1H NMR analysis and molecular conformation computation revealed that strong in tramolecular hydrogen bondings exist in dipyrrylmethane 4b and 4c (3 . 3' substituents are for mate and acetate esters),while very weak or no intramolecular hydrogen bonding exists in other dipyrrylmethanes.
Keywords:Dipyrrylmethane  Intramolecular hydrogen bonding  Chemical shift
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