Abstract
The rates of the aza-Michael reaction at room temperature were measured for some amines and alkenes. When the reaction mixture was diluted with methanol, the reaction was accelerated. The acceleration with methanol was especially strong for acrylonitrile. In the latter case, the reaction rate constant can increase by almost three decimal orders. The bulky substituent in the alpha position of methacrylates had little effect on the reaction rate, while the bulky substituent in the ester group significantly slowed the aza-Michael reaction.
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References
A. Yu. Rulev, Russ. Chem. Rev. 80, 197 (2011).
G. Cravotto, Y. Borretto, M. Oliverio, A. Procopio, and A. Penoni, Catal. Commun. 63, 2 (2015).
L. W. Xu, L. Li, and C. G. Xi, Helv. Chim. Acta 1, 522 (2004).
T. P. Loh and L. L. Wei, Synlett, No. 6, 975 (1998).
S. Kim, S. Kang, G. Kim, and Y. Lee, Org. Chem. 81, 4048 (2016).
O. V. Serdyuk, C. M. Heckel, and S. Tsogoeva, Org. Biomol. Chem. 11, 7051 (2013).
P. Chauhan, S. Mahajan, and D. Enders, Chem. Commun. 51, 12890 (2015).
K. K. Hii, Pure Appl. Chem. 78, 341 (2006).
G. Xu, T. Buechler, K. Wheeler, and H. Wang, Eur. J. 16, 2972 (2010).
X. F. Wang, J. An, X. X. Zhang, et al., Org. Lett. 13, 808 (2011).
B. L. Zhao, Y. Lin, H. H. Yan, and D. M. Du, Biomol. Chem. 13, 11351 (2015).
B. C. Ranu and S. Banerjee, Tetrahedron Lett. 48, 141 (2007).
Z. Feng, Q. L. Xu, L. X. Dai, and S. L. You, Heterocycles 80, 765 (2010).
S. Matsubara, M. Yoshioka, and K. Utimoto, Chem. Lett. 23, 827 (1994).
V. L. Plakidin and P. P. Gnatyuk, Zh. Org. Khim. 9, 167 (1973).
A. A. Gridnev, Polym. J. 24, 613 (1992).
A. J. Gordon and R. A. Ford, The Chemist’s Companion: A Handbook of Practical Data, Techniques and References (Mir, Moscow, 1975; Wiley, New York, 1972), rus. p. 167.
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Original Russian Text © E.V. Koverzanova, I.I. Levina, A.A. Gridnev, 2018, published in Khimicheskaya Fizika, 2018, Vol. 37, No. 2, pp. 11–18.
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Koverzanova, E.V., Levina, I.I. & Gridnev, A.A. Kinetics of the aza-Michael Reaction at Room Temperature. Russ. J. Phys. Chem. B 12, 46–52 (2018). https://doi.org/10.1134/S1990793118010219
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DOI: https://doi.org/10.1134/S1990793118010219