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分子內的Bradsher環化反應是指在酸催化下鄰酰基二芳基甲烷進行芳香環化脫氫生成蒽的反應。
反應機理:
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反應實例:
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另外Bradsher環加成反應是指乙烯基醚或乙烯基硫醚對吡啶鹽進行Diels–Alder加成的反應。
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參考文獻
1. (a) Bradsher, C. K. J. Am. Chem. Soc. 1940, 62, 486–488. Charles K. Bradsher was born in Petersburg, VA in 1912. After his Ph.D. under Louis F. Fieser at Harvard and postdoctoral training with R. C. Fuson, he became a professor at Duke University. (b)Bradsher, C. K.; Smith, E. S. J. Am. Chem. Soc. 1943, 65, 451–452. (c) Bradsher, C.K.; Vingiello, F. A. J. Org. Chem. 1948, 13, 786–789. (d) Bradsher, C. K.; Sinclair, E.F. J. Org. Chem. 1957, 22, 79–81.
2. Vingiello, F. A.; Spangler, M. O. L.; Bondurant, J. E. J. Org. Chem. 1960, 25, 2091–2094.
3. Brice, L. K.; Katstra, R. D. J. Am. Chem. Soc. 1960, 82, 2669–2670.
4. Saraf, S. D.; Vingiello, F. A. Synthesis 1970, 655.
5. Ahmed, M.; Ashby, J.; Meth-Cohn, O. J. Chem. Soc., Chem. Commun. 1970, 1094–1095.
6. Ashby, J.; Ayad, M.; Meth-Cohn, O. J. Chem. Soc., Perkin Trans. 1 1974, 1744–1747.
7. Bradsher, C. K. Chem. Rev. 1987, 87, 1277–1297. (Review).
8. Nicolas, T. E.; Franck, R. W. J. Org. Chem. 1995, 60, 6904–6911.
9. Magnier, E.; Langlois, Y. Tetrahedron Lett. 1998, 39, 837–840.
10. Urban, D.; Duval, E.; Langlois, Y. Tetrahedron Lett. 2000, 41, 9251–9256.
11. Soll, C. E.; Franck, R. W. Heterocycles 2006, 70, 531–540.
13. Mondal, M.; Kerrigan, N. J. Bradsher Reaction, In Name Reactions for Carbocyclic Ring Formations, Li, J. J., Ed.; Wiley: Hoboken, NJ, 2010, pp 251-266. (Review).
編譯自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Bradsher reaction,page 77-78.
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