Conclusions
Claisen rearrangements of bucharaine acetonide and its N-methyl derivative take place in the inlet system of a mass spectrometer at 90–110°C. At 180°C, an anomalous rearrangement is the main process, accompanied by the formation of dihydrofuranoquinolinone derivatives.
A similar process is observed in the γ, γ-dimethylallyl ethers of some hydroxyqinol-2-ones.
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Ya. V. Rashkes, Z. Sh. Faizutdinova, I. A. Bessonova, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 577 (1970).
E. N. Marvell, D. R. Anderson, and J. Ong., J. Org. Chem.,27, 1109 (1962); A. Jefferson and F. Scheinmann, Quart. Rev.,22, 391 (1968).
Ya. V. Rashkes, I. A. Bessonova, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 336 (1972).
I. A. Bessonova, Ya. V. Rashkes, and S. Yu. Yunusov, Khim. Prirodn. Soedin., 358 (1974).
R. Woodward and R. Hoffman, The Conservation of Orbital Symmetry, Academic Press, New York (1970); G. B. Gill, Quart. Rev., 22, 338 (1968).
B. D. Paul and P. K. Bose, J. Indian Chem. Soc.,45, 552 (1968); Indian J. Chem.,7, 678 (1969).
N. S. Vul'fson, V. I. Zaretskii, and V. G. Zaikin, Dokl. Akad. Nauk. SSSR,155, 1104 (1964).
V. N. Zvolinskii, M. E. Perel'son, and Yu. N. Sheinker, Teoret. Éksperim., Khim.,6, 250 (1970).
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Order of the Red Banner of Labor Institute of the Chemistry of Plant Substances of the Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 364–373, May–June, 1974.
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Rashkes, Y.V., Bessonova, I.A. & Yunusov, S.Y. Claisen rearrangement of alkoxyquinol-2-ones in mass spectrometry. Chem Nat Compd 10, 364–370 (1974). https://doi.org/10.1007/BF00563894
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DOI: https://doi.org/10.1007/BF00563894