Reactivities Involved in the Regioselectivity of Osazone Formation

Francisco Sánchez-Viesca^1, and Reina Gómez G¹

¹Department of Organic Chemistry, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City (CDMX), Mexico

Cite this paper:
Francisco Sánchez-Viesca and Reina Gómez G. Reactivities Involved in the Regioselectivity of Osazone Formation. World Journal of Organic Chemistry. 2017; 5(1):11-16. doi: 10.12691/wjoc-5-1-3

Abstract

The mechanism of osazone formation has been subject of many studies during a vast period of time. However, the regiochemistry related to osazones remained an unsolved problem until recently that we presented our theoretical findings that explain the factors that direct the regiochemistry of osazone formation. Now, we wish present to the teaching community this subject, as well as a discussion of an example of mixed osazone formation. This new topic includes the factors that conduce to the main product. This communication will fill a gap existing in the Organic Chemistry textbooks.

Keywords:
fructosazone hydrogen bonds 1 4-Hydrogen transfer internal oxido-reduction leaving groups Lewis bases

This work is licensed under a Creative Commons Attribution 4.0 International License. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/

Figures

References:

[1]	Sánchez-Viesca, F. and Gómez, R., “On the regiochemistry in the Heyns rearrangement”, Am. J. Chem., 5(3), 86-89, 2015.
[2]	Sánchez-Viesca, F. and Gómez, R., “On fructosazone regiochemistry”, Modern Chemistry, 4(1), 1.5, 2016.
[3]	Packer, J. and Vaughan, J., A Modern Approach to Organic Chemistry, Clarendon Press, Oxford, U. K., 1958, 479-482.
[4]	Weygand, F., “Amadori Umlagerungen”, Ber., 73(11), 1259-1278, 1940; Chem. Abstr., vol. 35, 3234-3235, 1941.
[5]	Wrodnigg, T. M. and Eder, B., “The Amadori and Heyns rearrangements”, Top. Curr. Chem., 215, 115-152, 2001.
[6]	Heyns, K. and Koch, W., “Formation of an amino sugar from D-fructose and ammonia”, Z. Naturforsch., 7b, 486-488, 1952; Chem. Abstr., vol. 47, 3392f, 1953.
[7]	Heyns, K. and Meinecke, K. H., “Über Bildung und Darstellung von d-Glucosamin aus Fructose und Ammoniak”, Chem. Ber., 86(11), 1453-1462, 1953; Chem. Abstr., vol. 49, 2333d, 1955.
[8]	Weygand, F., “Theorie der Osazonbildung”, Ber., 73(11), 1284-1291, 1940; Chem. Abstr., vol. 35, 3235, 1941.
[9]	Weygand, F. and Reckhaus, M., “Zur Theorie der Osazonbildung”, Chem. Ber., 82(4-5), 438-442, 1949; Chem. Abstr., vol. 44, 1911-1912, 1950.
[10]	Percival, E. G. V., “The structure and reactivity of the hydrazone and osazone derivatives of the sugars”, Adv. Carbohydr. Chem., 3, 23-44, 1948.
[11]	Hassner, A. and Catsoulacos, P., “On the mechanism of osazone formation”, Tetrahedron Lett., No.6, 489-493, 1967.
[12]	Metha, B. and Metha, M., Organic Chemistry, Prentice-Hall of India, 2005, 939.
[13]	Sears, C. and Wright, J. C., “The use of p-bromophenylhydrazine to determine the mechanism of osazone formation”, Proc. West Virginia Acad. Sci., 33, 78-80, 1961; Chem. Abstr., vol. 56, 10254g, 1962.
[14]	Shemyakin, M. M., Maimind, V. J., Ermolaev, K. M. and Bamdas, E. M., “The mechanism of osazone formation”, Tetrahedron, 21, 2771-2777, 1965.
[15]	McMurry, J., Química Orgánica, 8th. ed., Cengage Learning, Mexico, 2012, Apéndice B, Constantes de acidez, p. A-9.
[16]	Migrdichian, V., Organic Synthesis, Reinhold, New York, 1960, vol. I, 16
[17]	Compain, Ph., Gore, J. and Vatele, J. M., “Rearrangement of α-hydroxy imines to α-amino ketones: Mechanistic aspects and synthetic applications”, Tetrahedron, 52(19), 6647-6664, 1996.
[18]	Rappoport, Z., Ed., Handbook of tables for Organic Compound Identification, 3rd. ed., Chemical Rubber, Cleveland, 1967, 436-437.