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Addition of primaryN-nitroamides to activated olefins

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PrimaryN-nitrosulfamides readily undergo addition to acrolein and vinyl ketones to yieldN-γ-oxoalkyl-N-nitrosulfamides. The presence of a second substituent at the double bond hinders the reaction.N-Nitrourethane reacts with activated carbonyl compounds and α-nitroolefins.

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  1. 1.

    S. S. Novikov, G. A. Shvekhgeimer, V. V. Sevost'yanova, and V. A. Shlyapochnikov,Khimia alifaticheskikh i alitsiklicheskich nitrosoedinenii [Chemistry of Aliphatic and Alicyclic Nitrocompounds], Khimia, Moscow, 1974, 415 (in Russian).

  2. 2.

    O. A. Luk'yanov, V. P. Gorelik, V. A. Tartakovsky,Izy. Akad. Nauk, Ser. Khim., 1994, 94 [Russ. Chem. Bull., 1994,43, 89 (Engl. Transl.)].

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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1261–1263, July, 1994.

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Luk'yanov, O.A., Gorelik, V.P., Reshetova, O.S. et al. Addition of primaryN-nitroamides to activated olefins. Russ Chem Bull 43, 1197–1199 (1994). https://doi.org/10.1007/BF00698243

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Key words

  • N-nitrosulfamides
  • N-nitrourethane
  • N-γ-oxoalkyl-N-nitroamides
  • N-β-nitro-alkyl-N-nitrourethanes
  • N-γ-oxoalkyl-N-nitroamines
  • Michael-type reaction
  • activated olefins