Abstract
The reactions of 3-chloro-2-(polyfluoroalkyl)chromones with hydroxylamine in the presence of sodium acetate proceed with ring contraction to form benzofuran derivatives.
Similar content being viewed by others
References
V. Ya. Sosnovskikh, B. I. Usachev, and A. Yu. Sizov, Izv. Akad. Nauk, Ser. Khim., 2003, 484 [Russ. Chem. Bull., Int. Ed., 2003, 52, 508].
G. P. Ellis, Chromenes, Chromanones, and Chromones, in The Chemistry of Heterocyclic Compounds, Wiley, New York, 1977, 31.
V. Ya. Sosnovskikh, M. A. Barabanov, and A. Yu. Sizov, Izv. Akad. Nauk, Ser. Khim., 2002, 1184 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1280].
V. Ya. Sosnovskikh, A. Yu. Sizov, and B. I. Usachev, Izv. Akad. Nauk, Ser. Khim., 2002, 1175 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1270].
V. Ya. Sosnovskikh and B. I. Usachev, Izv. Akad. Nauk, Ser. Khim., 2000, 2109 [Russ. Chem. Bull., Int. Ed., 2000, 49, 2074].
J. R. Merchant and D. V. Rege, Tetrahedron, 1971, 27, 4837.
R. B. Gammill, S. A. Nash, and S. A. Mizsak, Tetrahedron Lett., 1983, 24, 3435.
Y. Sugita, T. Iwaki, M. Okamoto, and I. Yokoe, Heterocycles, 2001, 55, 881.
J.-P. Bouillon, A-M. Frisque-Hesbain, Z. Janousek, and H. G. Viehe, Heterocycles, 1995, 40, 661.
F. J. Weigert, J. Org. Chem., 1972, 37, 1314.
G. Shi and Y. Xu, J. Fluorine Chem., 1989, 44, 161.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sosnovskikh, V.Y., Usachev, B.I. & Sizov, A.Y. 2-(Polyfluoroalkyl)chromones. 15. Transformation of 3-chloro-2-(polyfluoroalkyl)chromones into benzofuran derivatives by hydroxylamine. Russian Chemical Bulletin 52, 984–988 (2003). https://doi.org/10.1023/A:1024425131436
Issue Date:
DOI: https://doi.org/10.1023/A:1024425131436