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Synthesis of enaminothiocarbonyl compounds (imidazolidine nitroxyl radicals) and their reactions with sodium hypobromite

  • Organic Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Reaction of 1-hydroxy-2,2,4,5,5-pentamethyl-3-imidazoline with thiocarboxylic acid derivatives in the presence of phenyllithium followed by oxidation affords enaminothiocarbonyl derivatives of imidazoline nitroxyl radicals.

  2. 2.

    Treatment of the enaminothiocarbonyl compounds with sodium hypobromite affords, depending on the substituent at the thiocarbonyl carbon atom, either acetylenic derivatives, or bromo-derivatives of the enaminocarbonyl compounds.

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Literature cited

  1. Ya. F. Freimanis, The Chemistry of Enaminoketones, Enaminoimines, and Enaminothiones [in Russian], Zinatne, Riga (1974), p. 274.

    Google Scholar 

  2. V. A. Reznikov, T. I. Reznikova, and L. B. Volodarskii, Izv. Sib. Otd., Akad. Nauk SSSR, Ser. Khim. Nauk, Issue 5, No. 12, 128 (1982).

    Google Scholar 

  3. W. Walter and T. Proll, Synthesis, 941 (1979).

  4. N. Kornblum and H. W. Pinnick, J. Org. Chem.,37, 2050 (1972).

    Google Scholar 

  5. L. B. Volodarskii, G. I. Shchukin, I. A. Grigor'ev, and N. N. Voronova, Izv. Akad. Nauk SSSR, Ser, Khim., 1434 (1987).

  6. V. A. Reznikov, T. I. Reznikova, and L. B. Volodarskii, Zh. Org. Khim.,18, 2135 (1982).

    Google Scholar 

  7. V. A. Reznikov and L. B. Volodarskii (Volodarsky), Tetrahedron Lett., 1625 (1986).

  8. A. Corsaro, A. Compagnini, U. Chiacchio, and G. Purello, Synthesis, 515 (1984).

  9. I. A. Grigor'ev, G. I. Shchukin, V. V. Martin, and V. I. Mamatyuk, Khim. Geterotsikl. Soedin., 252 (1985).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2585–2591, November, 1988.

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Reznikov, V.A., Volodarskii, L.B. Synthesis of enaminothiocarbonyl compounds (imidazolidine nitroxyl radicals) and their reactions with sodium hypobromite. Russ Chem Bull 37, 2331–2336 (1988). https://doi.org/10.1007/BF00959890

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  • DOI: https://doi.org/10.1007/BF00959890

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