Abstract
Isomerization of the acetates and benzoates of condensed hydroxy-substituted 2-trifluoromethyl-4H-pyran-4-ones at 300–320°C gave the corresponding derivatives of spiroannelated 3(2H)-furanones. Their structure was confirmed by spectral data and by X-ray crystallographic analysis.
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References
H. Paulsen,Advances in Carbohydrate Chemistry and Biochemistry (Eds. R. S. Tipson and D. Horton), Academic Press, New York, London,26, 127 (1971).
H. Paulsen,Methods of Investigation of Carbohydrates (Eds. R. L. Whistler and J. N. Bemiller) [Russian translation], Mir, Moscow (1975), p. 114.
J. C. Norrild, Ch. Pedersen, and J. Defaye,Carbohydr. Res.,291, 85 (1996).
L. V. Bakinovskii,Progress in the Chemistry of Carbohydrates (Ed. I. V. Torgov) [in Russian], Nauka, Moscow (1085), p. 7.
N. K. Kochetkov, V. M. Zhulin, E. M. Klimov, N. N. Malysheva, Z. G. Makarova, and A. Ya. Ott,Carbohydr. Res.,164, 241 (1987).
J. Defaye, A. Gadelle, and Ch. Pedersen,Carbohydr. Res.,205, 191 (1990).
A. Wisniewski, J. Gajdus, J. Sokolowski, and J. Szafranek,Carbohydr. Res.,114, 11 (1983).
V. I. Tyvorskii and D. N. Bobrov,Khim. Geterotsikl. Soedin., No. 8, 1138 (1997).
V. I. Tyvorskii and D. N. Bobrov,Khim. Geterotsikl. Soedin., No. 6, 780 (1998).
V. I. Tyvorskii, D. N. Bobrov, O. G. Kulinkovich, N. De Kimpe, and K. A. Tehrani,Tetrahedron,54, 2819 (1998).
V. I. Tyvorskii, L. S. Stanishevskii, and I. G. Tishchenko,Khim. Geterotsikl. Soedin., No. 7, 897 (1978).
F. M. Dean and M. V. Sargent,Comprehensive Heterocyclic Chemistry (Eds. A. R. Katritzky and Ch. W. Rees), Pergamon Press, Oxford, etc.,4, 579 (1984).
C. W. Bird and G. W. H. Cheeseman,Comprehensive Heterocyclic Chemistry (Eds. A. R. Katritzky and Ch. W. Rees), Pergamon Press, Oxford, etc.,4, 19 (1984).
V. Ya. Sosnovskikh, M. Yu. Mel'nikov, and V. A. Kutsenko,Izv. Akad. Nauk. Ser. Khim., No. 8, 1553 (1997).
F. H. Allen and O. Kennard,Chem. Design Automat. News,8, 31 (1993).
G. M. Sheldrick,SHELX-97. Program for Crystal Structure Refinement, University of Göttingen (1997).
G. M. Sheldrick,Acta Crystallogr.,A46, 467 (1990).
G. M. Sheldrick, Z. Dauter, K. S. Wilson, H. Hope, and L. Sieker,Acta Crystallogr.,D49, 18 (1993).
J. Cantocuzene and A. Keramat,Comp. Rend. Acad. Sci.,C264, 618 (1967).
Additional information
Belarus State University, Minsk; Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1028–1034, August, 2000.
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Bobrov, D.N., Lyakhov, A.S., Govorova, A.A. et al. Thermal rearrangement of condensed alkoxy-substituted 2-trifluoromethyl-4H-pyran-4-ones to spiroannelated 3(2H)-furanones. Chem Heterocycl Compd 36, 899–904 (2000). https://doi.org/10.1007/BF02256973
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DOI: https://doi.org/10.1007/BF02256973