Abstract
Bromination of β-aminovinyl ketones (AVK) with geminal arrangement of the fluoroalkyl and amino groups gives N-bromo derivatives. Regioisomeric AVK with the amino groups in the β-position relative to the fluoroalkyl group undergo bromination under analogous conditions to give a mixture of the α-bromo and α,N-dibromo derivatives. α-Bromo derivatives of AVK disproportionate upon storage.
Literature cited
Ya. F. Freimanis,Chemistry of Enaminoketones, Enaminoimines, and Enaminothiones [in Russian], Zinatne, Riga (1974), p. 201.
R. Fuson,Reactions of Organic Compounds [Russian translation], Mir, Moscow (1966).
V. I. Saloutin, Z. É. Skryabina, M. N. Rudaya, et al.,Izv. Akad. Nauk, Ser. Khim., No. 5, 1106 (1984).
K. I. Pashkevich and A. Ya. Aizikovich,Dokl. Akad. Nauk 244, 618 (1979).
K. I. Pashkevich, V. I. Filyakova, Yu. N. Sheinker, et al.,Izv. Akad. Nauk, Ser. Khim., No. 9, 2087 (1979).
Additional information
Division of Fine Chemical Synthesis, Institute of Organic Chemistry, Urals Branch, Russian Academy of Sciences, 620219 Ekaterinburg. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 3, pp. 746–749, March, 1992.
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Pashkevich, K.I., Filyakova, V.I. & Karpenko, N.S. Bromination of regioisomeric fluorine-containing β-aminovinyl ketones. Russ Chem Bull 41, 586–588 (1992). https://doi.org/10.1007/BF00863092
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DOI: https://doi.org/10.1007/BF00863092