Conclusions
-
1.
The Akabori reaction involves a stage in which an intermediate imine copper complex is formed from acetaldehyde and copper alaninate.
-
2.
The intermediate complex has a higher CH acidity than the initial alanine copper complex.
Similar content being viewed by others
Literature cited
M. Sato, K. Okawa, and S. Akabori, Bull. Chem. Soc. Japan,30, 937 (1957).
É. N. Safonova and V. M. Belikov, Usp. Khim.,36, 923 (1967).
V. M. Belikov, N. I. Kuznetsova, and É. N. Safonova, Khim. Prirodn. Soed., 31 (1967).
D. A. Buckingham, L. Q. Marzilli, and A. M. Sargeson, J. Amer, Chem. Soc.,89, 5133 (1967).
D. E. Metzler, Longenecker, J. B. Esmond, and E. Snell, J. Amer. Chem. Soc.,76, 639 (1954).
R. W. Layer, Chem. Rev.,63, 489 (1963); L. S. Povarov and B. M. Mikhailov, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 955 (1963).
G. L. Eichhorn and M. D. Marchand, J. Amer, Chem. Soc.,78, 2688 (1956).
J. Nakao, K. Sakauraix, and A. Nakahara, J. Chem. Soc. Japan,40, 1536 (1967).
Kaoru Harada and Jun-ichi Oh-Hashi, J. Organ. Chem.,32, 1103 (1967).
J. Sato, T. Takahashi, S. Imado, and N. Sugimoto, Yakugaku Zasshi,81, 819 (1961); Chem. Abst.,55, 24587e (1962).
Yu. M. Torchinskii and L. G. Koreneva, Biokhimiya,30, 39 (1965).
S. V. Vitt, M. B. Saporovskaya, and V. M. Belikov, Izv. Akad. Nauk SSSR, Ser. Khim., 277 (1967).
H. Mix and F. W. Wilcke, Hoppe Seylers Z. Phys. Chem.,337, 40 (1967).
R. E. Bowman and H. H. Strand, J. Chem. Soc., 1342 (1956).
I. M. Hays and C. Macek, Paper Chromatography [Russian translation], Izd. Inostr. Lit. (1962), p. 727 (D7).
Author information
Authors and Affiliations
Additional information
Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2536–2541, November, 1969.
Rights and permissions
About this article
Cite this article
Belikov, V.M., Vitt, S.V., Kuznetsova, N.I. et al. Reaction of the copper complex of L-alanine with acetaldehyde and the mechanism of the akabori reaction. Russ Chem Bull 18, 2371–2375 (1969). https://doi.org/10.1007/BF00906512
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00906512