On Fructosazone Regiochemistry

Francisco Sánchez-Viesca; Reina Gómez

doi:doi:10.11648/j.mc.20160401.11

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On Fructosazone Regiochemistry

Francisco Sánchez-Viesca, Reina Gómez

Published in Modern Chemistry (Volume 4, Issue 1)

Received: 20 January 2016 Accepted: 28 January 2016 Published: 19 February 2016

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Abstract

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.

Published in	Modern Chemistry (Volume 4, Issue 1)
DOI	10.11648/j.mc.20160401.11
Page(s)	1-5
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2016. Published by Science Publishing Group

Keywords

Fructosazone, Reaction Mechanisms, Reaction Intermediates, Regioselectivity, Retro-Amadori Rearrangement

References

[1]	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
[2]	J. Packer, and J. Vaughan, A Modern Approach to Organic Chemistry, Oxford, U. K.: Clarendon Press, 1958, pp. 479-482.
[3]	F. Weygand, “Theorie der Osazonbildung”, Ber., vol. 73(11), pp. 1284-1291, 1940; Chem Abstr., vol. 35, 3235, 1941.
[4]	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.
[5]	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.
[6]	A. Hassner, and P. Catsoulacos, “On the mechanism of osazone formation”, Tetrahedron Lett. No. 6, pp. 489-493, 1967.
[7]	T. M. Wrodnigg, and B. Eder, “The Amadori and Heyns rearrangements”, Top. Curr. Chem., vol. 215, pp. 115-152, 2001.
[8]	F. Weygand, “Amadori Umlagerungen”, Ber., vol. 73(11), pp. 1259-1278, 1940; Chem. Abstr., vol. 35, 3234-3235, 1941.
[9]	H. S. Isbell, and H. L. Frush, “Mutarotation, hydrolysis, and rearrangement reactions of glycosylamines”, J- Org. Chem., vol. 23(9), pp. 1309-1319, 1958.
[10]	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.
[11]	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.
[12]	J. F. Carson, “The reaction of fructose with isopropylamine and cyclohexylamine”, J. Am. Chem. Soc., vol. 77, pp. 1881-1884, 1955.
[13]	J. F. Carson, “The reaction of fructose with aliphatic amines”, J. Am. Chem. Soc., vol. 77, pp. 5957-5960, 1955.
[14]	B. Metha, and M. Metha, Organic Chemistry, Prentice-Hall of India, 2005, p. 939.
[15]	V. C. Barry, and E. W. D. Mitchell, “Mechanism of osazone formation”, Nature (London), vol. 175, p. 220, 1955.
[16]	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.
[17]	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.
[18]	E. M. Bamdas, K. M. Ermolaev, V. J. Maimind, and M. M. Shemyakin, “Mechanism of osazone formation”, Chem. & Ind. (London), 1959, pp. 1195-1196.
[19]	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.
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Francisco Sánchez-Viesca, Reina Gómez. (2016). On Fructosazone Regiochemistry. Modern Chemistry, 4(1), 1-5. https://doi.org/10.11648/j.mc.20160401.11

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ACS Style

Francisco Sánchez-Viesca; Reina Gómez. On Fructosazone Regiochemistry. Mod. Chem. 2016, 4(1), 1-5. doi: 10.11648/j.mc.20160401.11

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AMA Style

Francisco Sánchez-Viesca, Reina Gómez. On Fructosazone Regiochemistry. Mod Chem. 2016;4(1):1-5. doi: 10.11648/j.mc.20160401.11

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@article{10.11648/j.mc.20160401.11,
  author = {Francisco Sánchez-Viesca and Reina Gómez},
  title = {On Fructosazone Regiochemistry},
  journal = {Modern Chemistry},
  volume = {4},
  number = {1},
  pages = {1-5},
  doi = {10.11648/j.mc.20160401.11},
  url = {https://doi.org/10.11648/j.mc.20160401.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20160401.11},
  abstract = {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.},
 year = {2016}
}

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TY  - JOUR
T1  - On Fructosazone Regiochemistry
AU  - Francisco Sánchez-Viesca
AU  - Reina Gómez
Y1  - 2016/02/19
PY  - 2016
N1  - https://doi.org/10.11648/j.mc.20160401.11
DO  - 10.11648/j.mc.20160401.11
T2  - Modern Chemistry
JF  - Modern Chemistry
JO  - Modern Chemistry
SP  - 1
EP  - 5
PB  - Science Publishing Group
SN  - 2329-180X
UR  - https://doi.org/10.11648/j.mc.20160401.11
AB  - 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.
VL  - 4
IS  - 1
ER  -

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Author Information

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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Francisco Sánchez-Viesca, Reina Gómez. (2016). On Fructosazone Regiochemistry. Modern Chemistry, 4(1), 1-5. https://doi.org/10.11648/j.mc.20160401.11

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ACS Style

Francisco Sánchez-Viesca; Reina Gómez. On Fructosazone Regiochemistry. Mod. Chem. 2016, 4(1), 1-5. doi: 10.11648/j.mc.20160401.11

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AMA Style

Francisco Sánchez-Viesca, Reina Gómez. On Fructosazone Regiochemistry. Mod Chem. 2016;4(1):1-5. doi: 10.11648/j.mc.20160401.11

Copy | Download

@article{10.11648/j.mc.20160401.11,
  author = {Francisco Sánchez-Viesca and Reina Gómez},
  title = {On Fructosazone Regiochemistry},
  journal = {Modern Chemistry},
  volume = {4},
  number = {1},
  pages = {1-5},
  doi = {10.11648/j.mc.20160401.11},
  url = {https://doi.org/10.11648/j.mc.20160401.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20160401.11},
  abstract = {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.},
 year = {2016}
}

Copy | Download

TY  - JOUR
T1  - On Fructosazone Regiochemistry
AU  - Francisco Sánchez-Viesca
AU  - Reina Gómez
Y1  - 2016/02/19
PY  - 2016
N1  - https://doi.org/10.11648/j.mc.20160401.11
DO  - 10.11648/j.mc.20160401.11
T2  - Modern Chemistry
JF  - Modern Chemistry
JO  - Modern Chemistry
SP  - 1
EP  - 5
PB  - Science Publishing Group
SN  - 2329-180X
UR  - https://doi.org/10.11648/j.mc.20160401.11
AB  - 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.
VL  - 4
IS  - 1
ER  -

Copy | Download