Conclusions
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1.
Some 4- and 5-hydroxyketones were synthesized by the free-radical addition of alcohols toα,β-unsaturated ketones.
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2.
According to the data of the IR spectra, the 4-hydroxyketones exist in both the open and cyclic (hemiacetal) forms. The amount of the open form increases with increase in the steric hindrance in the cyclization step. The 5-hydroxyketones exist only in the open form.
Literature cited
V. G. Glukhovtsev, S. S. Spektor, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim., 2829 (1968).
V. G. Glukhovtsev, S. S. Spektor, and G. I. Nikishin, Izv. Akad. Nauk SSSR, Ser. Khim., 1592 (1969).
Yu. A. Pentin and I. S. Trubnikov, Dokl. Akad. Nauk SSSR,146, 107 (1962).
V. G. Glukhovtsev, G. I. Nikishin, S. S. Spektor, and S. V. Zakharova, Izv. Akad. Nauk SSSR, Ser. Khim., 1605 (1968).
T. I. Temnikova, Course in Theoretical Organic Chemistry [in Russian], Khimiya, Leningrad (1968), p. 210.
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Translated from, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 698–700, March, 1973.
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Niklshin, G.I., Glukhovtsev, V.G., Spektor, S.S. et al. Free-radical addition of alcohols toα, β-unsaturated ketones and tautomerism of formed 4-hydroxyketones. Russ Chem Bull 22, 684–686 (1973). https://doi.org/10.1007/BF00854067
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DOI: https://doi.org/10.1007/BF00854067