Perkow磷酸烯基酯的合成
由α-卤代羰基化合物和三烷基亚磷酸酯制备磷酸烯基酯的反应。仲或叔卤代物由于位阻较难发生Michaelis-Arbuzov反应。
反应机理
反应实例
参考文献
1. Perkow, W.; Ullrich, K.; Meyer, F. Nasturwiss. 1952, 39, 353.
2. Perkow, W. Ber. Dtsch. Chem. Ges. 1954, 87, 755.
3. Borowitz, G. B.; Borowitz, I. J. Handb. Organophosphorus Chem. 1992, 115.
(Review).
4. Hudson, H. R.; Matthews, R. W.; McPartlin, M.; Pryce, M. A.; Shode, O. O. J. Chem. Soc., Perkin Trans. 2 1993, 1433.
5. Janecki, T.; Bodalski, R. Heteroat. Chem. 2000, 11, 115.
6. Balasubramanian, M. Perkow Reaction, in Name Reactions for Functional Group Transformations, Li, J. J. Ed., Wiley: Hoboken, NJ, 2007, pp 369-385. (Review).
7. Coffinier, D.; El Kaim, L.; Grimaud, L. Org. Lett. 2009, 11, 1825–1827.
8. Huras, B.; Konopski, L.; Zakrzewski, J. J. Labeled Compd. Radiopharm. 2011, 54, 399–400.
9. Yavari, I.; Hosseinpour, R.; Pashazadeh, R.; Ghanbari, E.; Skoulika, S. Tetrahedron 2013, 69, 2462–2467.
编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Perkow vinyl phosphate synthesis，page 470-471.
Michaelis-Arbuzov膦酸酯合成
2016-10-31 有机合成
亚磷酸酯和卤代烷反应得到膦酸酯。
反应机理
反应实例
过渡金属催化偶联得到产物，而不是SN2。
参考文献
1. (a) Michaelis, A.; Kaehne, R. Ber. 1898, 31, 10481055. (b) Arbuzov, A. E. J. Russ.Phys. Chem. Soc. 1906, 38, 687.
2. Surmatis, J. D.; Thommen, R. J. Org. Chem. 1969, 34, 559-560.
3. Gillespie, P.; Ramirez, F.; Ugi, I.; Marquarding, D. Angew. Chem. Int. Ed. 1973, 12, 91-119. (Review).
4. Waschbűsch, R.; Carran, J.; Marinetti, A.; Savignac, P. Synthesis 1997, 727-743.
5. Bhattacharya, A. K.; Stolz, F.; Schmidt, R. R. Tetrahedron Lett. 2001, 42, 5393-5395.
6. Erker, T.; Handler, N. Synthesis 2004, 668-670.
7. Souzy, R.; Ameduri, B.; Boutevin, B.; Virieux, D. J. Fluorine Chem. 2004, 125,
1317-1324.
8. Kadyrov, A. A.; Silaev, D. V.; Makarov, K. N.; Gervits, L. L.; Röschenthaler, G.-V. J. Fluorine Chem. 2004, 125, 1407-1410.
9. Ordonez, M.; Hernandez-Fernandez, E.; Montiel-Perez, M.; Bautista, R.; Bustos, P.;Rojas-Cabrera, H.; Fernandez-Zertuche, M.; Garcia-Barradas, O. Tetrahedron: Asymmetry 2007, 18, 2427-2436.
10. Piekutowska, M.; Pakulski, Z. Carbohydrate Res. 2008, 343, 785-792.
11. Dhokale, R. A.; Mhaske, S. B. Org. Lett. 2013, 15, 2218–2221.
编译自：Name Reactions （A Collection of Detailed Reaction Mechanisms）, Jie Jack Li, Michaelis-Arbuzov phosphonate synthesis，page 399-400.