On Fructosazone Regiochemistry
Modern Chemistry
Volume 4, Issue 1, February 2016, Pages: 1-5
Received: Jan. 20, 2016; Accepted: Jan. 28, 2016; Published: Feb. 19, 2016
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Francisco Sánchez-Viesca, Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City, México
Reina Gómez, Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City, México
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The regiochemistry observed in fructosazone has not been explained by other authors. A novel reaction mechanism has been provided in order to explain the regioselectivity leading to the fructosazone molecule. Our proposal and subsequent reactions are in agreement with the experimental facts and with well known reactivities. So, we have eliminated the existing gap between fact and theory. Many years have elapsed before an answer was given at last.
Fructosazone, Reaction Mechanisms, Reaction Intermediates, Regioselectivity, Retro-Amadori Rearrangement
To cite this article
Francisco Sánchez-Viesca, Reina Gómez, On Fructosazone Regiochemistry, Modern Chemistry. Vol. 4, No. 1, 2016, pp. 1-5. doi: 10.11648/j.mc.20160401.11
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This article is an open access article distributed under the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
F. Sánchez-Viesca, and R. Gómez, “On the regiochemistry in the Heyns rearrangement”, Am. J. Chem., vol. 5(3), pp. 86-89, 2015. DOI: 10.5923/j.chemistry.20150503.03
J. Packer, and J. Vaughan, A Modern Approach to Organic Chemistry, Oxford, U. K.: Clarendon Press, 1958, pp. 479-482.
F. Weygand, “Theorie der Osazonbildung”, Ber., vol. 73(11), pp. 1284-1291, 1940; Chem Abstr., vol. 35, 3235, 1941.
F. Weygand, and M. Reckhaus, “Zur Theorie der Osazonbildung”, Chem. Ber., vol. 82(4-5), pp. 438-442, 1949; Chem. Abstr., vol. 44, 1911-1912, 1950.
E. G. V. Percival, “The structure and reactivity of the hydrazone and osazone derivatives of the sugars”, Adv. Carbohydr. Chem., vol. 3, pp. 23-44, 1948.
A. Hassner, and P. Catsoulacos, “On the mechanism of osazone formation”, Tetrahedron Lett. No. 6, pp. 489-493, 1967.
T. M. Wrodnigg, and B. Eder, “The Amadori and Heyns rearrangements”, Top. Curr. Chem., vol. 215, pp. 115-152, 2001.
F. Weygand, “Amadori Umlagerungen”, Ber., vol. 73(11), pp. 1259-1278, 1940; Chem. Abstr., vol. 35, 3234-3235, 1941.
H. S. Isbell, and H. L. Frush, “Mutarotation, hydrolysis, and rearrangement reactions of glycosylamines”, J- Org. Chem., vol. 23(9), pp. 1309-1319, 1958.
K. Heyns, and W. Koch, “Formation of an amino sugar from D-fructose and ammonia”, Z. Naturforsch., vol. 7b, pp. 486-488, 1952; Chem. Abstr., vol. 47, 3392f, 1953.
K. Heyns, and K. H. Meinecke, “Über Bildung und Darstellumg von d-Glucosamin aus Fructose und Ammoniak”, Chem. Ber., vol. 86(11), pp. 1453-1462, 1953; Chem. Abstr., vol. 49, 2333d, 1955.
J. F. Carson, “The reaction of fructose with isopropylamine and cyclohexylamine”, J. Am. Chem. Soc., vol. 77, pp. 1881-1884, 1955.
J. F. Carson, “The reaction of fructose with aliphatic amines”, J. Am. Chem. Soc., vol. 77, pp. 5957-5960, 1955.
B. Metha, and M. Metha, Organic Chemistry, Prentice-Hall of India, 2005, p. 939.
V. C. Barry, and E. W. D. Mitchell, “Mechanism of osazone formation”, Nature (London), vol. 175, p. 220, 1955.
H. Simon, H. D. Dorrer, and A. Trebst, “Untersuchungen über den Mechanismus der Osazonbildung in der Zuckerreihe”, Chem. Ber., vol. 96, pp. 1285-1288, 1963; Chem. Abtr., vol 59, 2918g, 1963.
C. Sears, and J. C. Wright, “The use of p-bromophenyl-hydrazine to determine the mechanism of osazone formation”, Proc. West Virginia Acad. Sci., vol 33, pp. 78-80, 1961; Chem. Abstr., vol. 56, 10254g, 1962.
E. M. Bamdas, K. M. Ermolaev, V. J. Maimind, and M. M. Shemyakin, “Mechanism of osazone formation”, Chem. & Ind. (London), 1959, pp. 1195-1196.
M. M. Shemyakin, V. J. Maimind, K. M. Ermolaev, and E. M. Bamdas, “The mechanism of osazone formation”, Tetrahedron, vol. 21, pp. 2771-2777, 1965.
J. McMurry, Química Orgánica, 8th. ed., México: Cengage Learning, 2012, Apéndice B, Constantes de acidez, p. A-9.
V. Migrdichian, Organic Synthesis, New York: Reinhold, 1960, vol 1, p. 16.
Ph. Compain, J. Gore, and J. M. Vatele, “Rearrangement of α-hydroxy imines to α-amino ketones: Mechanistic aspects and synthetic applications”, Tetrahedron, vol. 52(19), pp. 6647-6664, 1996.
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