Summary
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1.
A method was developed for the synthesis of aryl 2-nitrovinyl ketones (3-nitroacrylophenones) (Ar=C6H5, p-CH3C6H4, and p-BrC6H4.
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2.
A study was made of the reactions of these compounds with nucleophilic reagents (OCH −3 , CH3OH, OH−).
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3.
The possible mechanism of these reactions is discussed.
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Literature cited
B. J. Cramer, W. Schoeder, W. J. Morgan, C. H. Nield, M. Edwards, C. J. Jarowski, and B. Puetrer, J. Amer. Pharm. Assoc.37, 439 (1948).
M. M. Fraser and R. A. Raphael, J. Chem. Soc. 2245 (1950).
A. N. Nesmeyanov and M. I. Rybinskaya, Dokl. AN SSSR120, 793 (1958).
A. N. Nesmeyanov, L. V. Rybin, and M. I. Rybinskaya, Izv. AN SSSR. Otd. khim. n 1451 (1961).
A. N. Nesmeyanov, M. I. Rybinskaya, and L. V. Rybin, Izv. AN SSSR, Otd. khim. n. 2152 (1961).
H. Shechter, F. Conrad, A. L. Daulton, and R. B. Kaplan, J. Amer. Chem. Soc.74, 3052 (1952).
A. N. Nesmeyanov and M. I. Rybinskaya, Dokl. AN SSSR115, 315 (1957).
A. N. Nesmeyanov and M. I. Rybinskaya, Izv. AN SSSR. Otd. khim. n. 816 (1962).
S. I. Miller and P. K. Yonan, J. Amer. Chem. Soc.79, 5931 (1957).
N. K. Kochetkov, E. E. Nifant'ev, and S. D. Sokolov, Zh. obshch. khimii29, 2570 (1959).
A. N. Nesmeyanov, L. A. Kazatsyna, N. K. Kochetkov, and M. I. Rybinskaya, Izv. AN SSSR. Otd. khim. n. 784 (1954).
S. Patai and Z. Rappoport, J. Chem. Soc. 392 (1962).
F. H. Pechman, Ber.15, 86 (1882).
K. V. Auwers, Ber.50, 1177 (1917).
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Rybinskaya, M.I., Rybin, L.V. & Nesmeyanov, A.N. Synthesis of aryl 2-nitrovinyl ketones [3-nitroacrylophenones], and the reactions of these compounds with nucleophilic reagents. Russ Chem Bull 12, 810–815 (1963). https://doi.org/10.1007/BF01134731
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DOI: https://doi.org/10.1007/BF01134731