Synthesis of new 3-(2,2,2-trifluoroethyl)-5-hydroxy-5-(phenylsulfanyl- or phenylsulfonyl-methyl)-1,5-dihydropyrrol-2-ones starting from alpha,beta-unsaturated gamma-lactones and primary amines

Bouillon, Jean-Philippe;Shermolovich, Yuriy;Mykhaylychenko, Sergiy;Harakat, Dominique;Tinant, Bernard
(2007) Journal of Fluorine Chemistry — Vol. 128, n° 8, p. 931-937 (2007)

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Authors
  • Bouillon, Jean-Philippe
    Author
  • Shermolovich, Yuriy
    Author
  • Mykhaylychenko, Sergiy
    Author
  • Harakat, Dominique
    Author
  • Tinant, BernardUCLouvain
    Author
Abstract
The paper presents an efficient and straightforward transformation of alpha,beta-unsaturated gamma-lactones into 2,2,2-trifluoroethyl substituted gamma-lactams, starting from a variety of primary amines. The structures of all new compounds were ascribed using 1D NMR (F-19, H-1, C-13), IR, MS. Selected 19F, 13 C NMR and IR data of gamma-lactams were compared to those of one which was characterized by X-ray diffraction analysis. The possible mechanism for the formation of gamma-lactams is also presented. (c) 2007 Elsevier B.V. All rights reserved.
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Bouillon, J.-P., Shermolovich, Y., Mykhaylychenko, S., Harakat, D., & Tinant, B. (2007). Synthesis of new 3-(2,2,2-trifluoroethyl)-5-hydroxy-5-(phenylsulfanyl- or phenylsulfonyl-methyl)-1,5-dihydropyrrol-2-ones starting from alpha,beta-unsaturated gamma-lactones and primary amines. Journal of Fluorine Chemistry, 128(8), 931-937. https://doi.org/10.1016/j.jfluchem.2007.03.020 (Original work published 2007)