| 带有致钝取代基的萘衍生物和SO3的反应研究 |
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| 引用本文： | 邹友思,林静.带有致钝取代基的萘衍生物和SO3的反应研究[J].高等学校化学学报,1995,16(11):1727-1730. |
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| 作者姓名： | 邹友思 林静 |
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| 作者单位： | 厦门大学化学系, 厦门, 361005 |
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| 基金项目： | 国家教育委员会留学回国人员科研经费资助 |
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| 摘 要： | 研究了一系列带有醛基、苯甲酮基、羧基、酯基和硝基等致钝取代基的萘衍生物与SO3的反应。1-萘甲醛的单磺化得到比例为55:9:6:30的5-、6-、7-和8-磺酸取代物。1-苯甲酮萘则以83:11:6的比例得到5-、6-和7-磺酸取代物。1-硝基萘专一地得到5位磺化产物,1-萘甲酸和1-萘甲酸甲酯得到5位和8位取代产物。所有的2位取代萘衍生物均先得到5和8位取代产物,在过量磺化中生成的主产物为5,7-二磺酸取代物,提出了生成SO3络合物及迫位磺化的历程,报道了8-磺酸-1-萘甲酸酐的物理数据。
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| 关 键 词： | 钝化萘衍生物 三氧化硫 磺化反应 |
| 收稿时间： | 1994-11-14 |
The Reaction of Deactivated Napthalene Derivatives with Sulfur Trioxide |
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| ZOU You-Si,LIN Jing.The Reaction of Deactivated Napthalene Derivatives with Sulfur Trioxide[J].Chemical Research In Chinese Universities,1995,16(11):1727-1730. |
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| Authors: | ZOU You-Si LIN Jing |
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| Institution: | Department of Chemistry, Xiamen University, Xianien, 361005 |
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| Abstract: | The reaction of sulfur trioxide with deactivated naphthalene derivatives containing an electron withdrawing substituent, viz. CHO, COPh, CO2H, and CO2Me, indichloromethane as the solvent has been studied by analysis of the resulting mixtures of the sulfo derivatives with 1HNMR,Monosulfonation of 1-formylnaphthalene yields 5-S,6-S,7-Sand 8-S, in a 55: 9:6: 30 ratio, that of 1-benzoylnaphthalene 5-S,6-Sand 7-S in a ratio of 83 : 11: 6, and 1-nitronaphthalene only 5-S. 1-Naphthoic acid and its methyl ester upon SO3 sulfonation and aqueous work-up both yield 5-and 8-sulfonaphthoic acid in a ratio of 65 : 35 and 77: 21 respectively. The initially formed peri substituted product is the intramolecular anhydride of 8-sulfo-1-naphthoic acid. All the 2-substituted naphthalenes upon SO3 sulfonation yield 505and 8 S. |
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| Keywords: | Deactivated naphthalene derivatives Sulfo trioxide Sulfonation |
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