Abstract
The reaction of propynals X-C≡C-CHO, where X = Alk or Ar, with 2,3-di(N-hydroxyamino)-2,3-dimethylbutane gives exclusively 1-X-2-(1-hydroxy-4,4,5,5-tetramethylimidazolidin-2-ylidene)ethanones. In the case of X = Me3Si, the reaction affords 2-(2-trimethylsilylethynyl)-4,4,5,5-tetramethylimidazolidine-1,3-diol. The reaction of propynal containing X = Et3Ge yields both types of the products. The resulting imidazolidine-1,3-diol can be quantitatively isomerized to imidazolidin-2-ylideneethanone, oxidized to 2-[2-(triethylgermyl)ethynyl]-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl, or transformed into ethynyl-substituted nitronyl nitroxide.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
E. Tretyakov, G. Romanenko, A. Podoplelov, V. Ovcharenko, Eur. J. Org. Chem., 2006, 2695.
E. V. Tretyakov, G. V. Romanenko, V. I. Ovcharenko, Izv. Akad. Nauk, Ser. Khim., 2006, 570 [Russ. Chem. Bull., Int. Ed., 2006, 55, 591].
E. V. Tretyakov, A. V. Tkachev, T. V. Rybalova, Yu. V. Gatilov, D. W. Knight, S. F. Vasilevsky, Tetrahedron, 2000, 56, 10075.
V. A. Reznikov, G. I. Roshchupkina, D. G. Mazhukin, P. A. Petrov, S. A. Popov, S. V. Fokin, G. V. Romanenko, T. V. Rybalova, Yu. V. Gatilov, Yu. G. Shvedenkov, I. G. Irtegova, L. A. Shundrin, V. I. Ovcharenko, Eur. J. Org. Chem., 2004, 749.
B. Bleaney, K. D. Bowers, Proc. Roy. Soc., 1952, A214, 451.
E. Tretyakov, G. Romanenko, V. Ikorskii, D. Stass, V. Vasiliev, M. Demina, A. Mareev, A. Medvedeva, E. Gorelik, V. Ovcharenko, Eur. J. Org. Chem., 2007, 3639.
M. M. Demina, A. S. Medvedeva, N. I. Protsuk, N. S. Vyazankin, Zh. Obshch. Khim., 1978, 48, 1563 [J. Gen. Chem. USSR, 1978, 48, 1432 (Engl. Transl.)].
V. I. Ovcharenko, S. V. Fokin, G. V. Romanenko, I. V. Korobkov, P. Ray, Izv. Akad. Nauk, Ser. Khim., 1999, 1539 [Russ. Chem. Bull., 1999, 48, 1519 (Engl. Transl.)].
C. Hirel, K. E. Vostrikova, J. Pécaut, V. I. Ovcharenko, P. Rey, Chem. Eur. J., 2001, 7, 2007.
Organic Syntheses. An Annual Publication of Satisfactory Methods for the Preparation of Organic Chemicals, New York, Annual vol. 20–25, 1940–1945.
F. B. Sviridenko, D. V. Stass, T. V. Kobzeva, E. V. Tretyakov, S. V. Klyatskaya, E. V. Mshvidobadze, S. F. Vasilevsky, Yu. N. Molin, J. Am. Chem. Soc., 2004, 126, 2807.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 588–594, March, 2008.
Rights and permissions
About this article
Cite this article
Tretyakov, E.V., Romanenko, G.V., Stass, D.V. et al. Key influence of the nature of the substituent in the propynal molecule on the outcome of its reaction with vicinal di(N-hydroxyamine). Russ Chem Bull 57, 601–607 (2008). https://doi.org/10.1007/s11172-008-0094-8
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-008-0094-8