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在碱性条件下邻羟基芳基酮和芳基甲酸酐反应制备黄酮和异黄酮的反应。反应机理和Kostanecki反应(饱和酸酐作为底物)类似。
反应机理
反应实例
【J. Org. Chem. 1987, 52, 4702–4709】
【Russ. J. Bioorg. Chem. 2006, 32, 277–279】
【Bioorg. Med. Chem. Lett. 2008,16, 4064–4074】
【Bioorg. Med. Chem. Lett. 2008,16, 4064–4074】
Robert Robinson (United Kingdom, 1886-1975) won the Nobel Prize in Chemistry in 1947 for his studies on alkaloids. However, Robinson himself considered his greatest contribution to science was that he founded the qualitative theory of electronic mechanisms in organic chemistry. Robinson, along with Lapworth (a friend) and Ingold (a rival), pioneered the arrow pushing approach to organic reaction mechanism. Robinson was also an accomplished pianist. James Allan, his student, also coauthored another important paper with Robinson on the relative directive powers of groups for aromatic substitution.
【 Robert Robinson (英国人, 1886-1975)由于和其学生在生物碱方面的研究获得1947年的诺贝尔化学奖。但他自己认为他最大的贡献是发现了有机化学机理的等量电子理论。Robinson,他的一个朋友 Lapworth和其竞争对手 Ingold共同开创了有机化学机理用箭头表示电子转移的方法。Robinson 也是一个很专业的钢琴家。James Allan是Robinson的学生,他和Robinson共同发表了另外一个很重要的论文,其中介绍了有关芳基取代定位的研究。】
参考文献
1. Allan, J.; Robinson, R. J. Chem. Soc. 1924, 125, 2192–2195.
2. Széll, T.; Dózsai, L.; Zarándy, M.; Menyhárth, K. Tetrahedron 1969, 25, 715–724.
3. Wagner, H.; Maurer, I.; Farkas, L.; Strelisky, J. Tetrahedron 1977, 33, 1405–1409.
4. Dutta, P. K.; Bagchi, D.; Pakrashi, S. C. Indian J. Chem., Sect. B 1982, 21B, 1037–1038.
5. Patwardhan, S. A.; Gupta, A. S. J. Chem. Res., (S) 1984, 395.
6. Horie, T.; Tsukayama, M.; Kawamura, Y.; Seno, M. J. Org. Chem. 1987, 52, 4702–4709.
7. Horie, T.; Tsukayama, M.; Kawamura, Y.; Yamamoto, S. Chem. Pharm. Bull. 1987,35, 4465–4472.
8. Horie, T.; Kawamura, Y.; Tsukayama, M.; Yoshizaki, S. Chem. Pharm. Bull. 1989,37, 1216–1220.
9. Poyarkov, A. A.; Frasinyuk, M. S.; Kibirev, V. K.; Poyarkova, S. A. Russ. J. Bioorg.Chem. 2006, 32, 277–279.
10. Peng, C.-C.; Rushmore, T.; Crouch, G. J.; Jones, J. P. Bioorg. Med. Chem. Lett. 2008,16, 4064–4074.
11. Levchenko, K. S.; Semenova, I. S.; Yarovenko, V. N.; Shmelin, P. S.; Krayushkin, M.M. Tetrahedron Lett. 2012, 53, 3630–3632。
编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Allan–Robinson reaction,page 8-9.
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