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化学学报
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化学学报 ›› 1997, Vol. 55 ›› Issue (6): 605-610. 上一篇    下一篇

研究论文

富烯与2-吡啶甲基锂及2-喹啉甲基锂的反应: 含氮杂环取代二茂 铁的合成

贺峥杰;舒学军;陈寿山   

  1. 南开大学元素有机化学研究所.天津(300071)
  • 发布日期:1997-06-15

Reactions of 6, 6-dialkylfulvenes with 6-methyl-2- pyridylmethyllithium and 2-quinolylmethyllithium

He Zhengjie;Shu Xuejun;Chen Shoushan   

  1. Nankai Univ, Elementoorgan Chem Lab.Tianjin(300071)
  • Published:1997-06-15

PDF

324

被引次数

2

在四氢呋喃-乙醚溶剂中,6-甲基-2-吡啶甲基锂与6,6-二烷基富烯或6,6-n亚甲基富烯(n=4,5,6)均发生环外双键加成反应。在类似反应条件下,2-喹啉甲基锂与6-甲基-6-乙基富烯或6,6-五亚甲基富烯皆发生加成反应和α-攫氢的竞争反应。用上述反应产生的取代环戊二烯基锂与二氯化铁配位,合成了一系列含氮杂环取代二茂铁衍生物。其结构经^1HNMR,元素分析和MS确证。在该类化合物的质谱裂解中,发现吡啶环对铁原子存在配位作用。

关键词: 二茂铁, 氮杂环, 甲基锂, 吡啶甲基, 富烯, 加成反应, 二烷基富烯, 四氢呋喃, 二茂铁衍生物

In mixed tetrahydrogenfuran-ether solvent, exocyclc double bond addition reactions of 6, 6-dialkylfulvenes or 6, 6- polymethylenefulvenes take place with 6-methyl-2-pyridylmethyllithium. When 6-methyl-6-ethylfulvene or 6, 6-pentamethylenefulvene reacts with 2-quinolylmethyllithium under similar conditions, addition and α -hydrogen abstract occur competitively. A series of nitrogen- heterocyclic substituted ferrocene derivatives have been synthesized by complexation of substituted cyclopentadienyllithium obtained in above reactions with FeCl~2. Their structures have been characterized by ^1H NMR, elemental analysis and mass spectra. In their MS breakdown mechanism, coordination of pyridyl moiety to iron atom is proposed.

Key words: FERROCENE, LITHIUM METHIDE, PICOLYL, FULVENE, ADDITION REACTION, TETRAHYDROFURAN

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