高等学校化学学报

高等学校化学学报 ›› 2002, Vol. 23 ›› Issue (5): 839.

• 研究论文 • 上一篇    下一篇

膦、胂叶立德的化学与应用(ⅩⅩⅨ)──含全氟烷基胂叶立德水解合成2-吡喃酮衍生物

曹卫国1,2, 丁维钰1, 汪丽燕1, 宋力平1, 张倩影1   

  1. 1. 上海大学化学系, 上海 201800;
    2. 中国科学院上海有机化学研究所金属有机开放实验室, 上海 200032
  • 收稿日期:2001-02-05 出版日期:2002-05-24 发布日期:2002-05-24
  • 通讯作者: 曹卫国(1962年出生),男,教授,主要从事元素有机化合物合成与应用的研究.E-mail:caoweig@online.sh.cn E-mail:caoweig@online.sh.cn
  • 基金资助:

    国家自然科学基金(批准号:29772021);上海市自然科学基金资助.

Chemistry and Applications of Phosphonium and Arsonium Ylides(ⅩⅩⅨ)──Studies on the Hydrolysis of Arsonium Ylides Containing Perfluoroalkyl Group andSynthesis of2-Pyranone Derivatives

CAO Wei-Guo1,2, DING Wei-Yu1, WANG Li-Yan1, SONG Li-Ping1, ZHANG Qian-Ying1   

  1. 1. Department of Chemistry, Shanghai University, Shanghai 200436 China;
    2. Laboratory of Organometallic Chemistry Shanghai Organic Chemistry Institute, Academia Sinica, Shanghai 200032, China
  • Received:2001-02-05 Online:2002-05-24 Published:2002-05-24

PDF (PC)

被引次数

2

摘要： 在无水碳酸钾存在下,以无水二氯甲烷作溶剂,室温下将溴化(2－萘甲酰基)甲基三苯基鉮(1)与2－全氟炔酸甲酯(2)反应,高产率地得到加合产物4-(2－萘甲酰基)－2－三苯基胂基－3－全氟烷基－3－丁烯酸甲酯(3)和少量4－(2－萘甲酰基)－4－三苯基胂基－3－全氟烷基－2－丁烯酸甲酯(4).加合产物3在9:1的甲醇－水溶液中在一定温度下反应,高产率地得到4-全氟烷基－6－(2－萘基)－2－吡喃酮(5).研究发现硅胶对该反应具有催化作用.提出并讨论了反应机理.

关键词: 胂叶立德, 水解, 2－吡喃酮衍生物

Abstract: In the presence of K2CO3, reaction of (2-naphthoyl)methyl arsonium bromide (1) with methyl2-perfluoroalkynoates(2) in methylene chloride at room temperature afforded the adduct methyl4-(2-naphthoyl)-2-triphenylarsoranylidene-3-perfluoroalkyl-3-butenoates(3) as major product and 4-(2-naphthoyl)-4-triphenylarsoranylidene-3-perfluoroalkyl-2-butenoat.es (4) as minor product in high yield.Hydrolysis of compound 3 in V(CH3OH):V(CH2O) = 9:1 methanolic solution at 80 in a sealed tube,4-perfluoroalkyl-6-(2-naphthyl)-2-pyranones(5) was obtained in an excellent yield.The catalytic hydroly-sis of compound 3 with silica gel and the mechanisms for the formation of the products will also be discuss-ed.

Key words: Arsonium ylide, Hydrolysis, 2-Pyranone derivatives

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