Volume 7, Issue 1, March 2019, Pages: 18-26
Received: Feb. 7, 2019;
Accepted: Mar. 18, 2019;
Published: Apr. 13, 2019
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Francisco Sánchez-Viesca, Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City (CDMX), México
Martha Berros, Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City (CDMX), México
Reina Gómez, Organic Chemistry Department, Faculty of Chemistry, National Autonomous University of Mexico, Mexico City (CDMX), México
This Review is a brief account of our theoretical contributions in seven research communications in the field of reaction mechanisms. Some mechanisms were corrected as in the case of the Baeyer-Drewsen indigo synthesis. When two very different reaction mechanisms had been proposed, as in the Clemmensen Reduction, a unified theory was provided. In other cases there were no reaction mechanisms at all, as in the Baeyer-Emmerling synthesis of indigo and in the Froehde Reaction for opioids. This deficit has been solved. The reaction that controls fructosazone regiochemistry has been described, and an internal process in a mixed osazone formation has been explained. All the proposals are based on well known reactivities and we provide complete and coherent reaction series with commented steps.
Recent Advances in Several Organic Reaction Mechanisms, Modern Chemistry.
Vol. 7, No. 1,
2019, pp. 18-26.
Baeyer-Drewson indigo synthesis, https://en.wikipedia.org/wiki/baeyer-drewson_indigo_synthesis Accessed: Feb. 4, 2019.
I. Tanasescu, and A. Georgescu, “Sur le mécanisme de formation de l’indigo, dans la synthèse de v. Baeyer”, Bull. Soc. Chim. France, vol. 51, pp. 234-240, 1932.
S. Ranganathan, “The story of indigo”, Resonance-Journal of Science Education (Bangalore, India), vol. 1(8), pp. 22-26, 1996.
F. Sánchez-Viesca, M. Berros, and R. Gómez, “On the mechanism of the Baeyer-Drewsen synthesis of indigo”, Am. J. Chem., vol. 6(1), pp. 18-22, 2016.
I. T. Millar, A shorter Sidgwick’s Organic Chemistry on Nitrogen, Oxford, UK: Clarendon, 1969, p. 322.
V. Migrdichian, Organic Synthesis, New York, USA: Reinhold, 1960, vol. 2, pp. 1631-1632.
G. Hilgetag, and A. Martini, Eds., Weygand-Hilgetag Preparative Organic Chemistry, New York, USA: Wiley, 1972, pp. 447-448.
Tomasz Dolinowski, Clemmensen reduction mechanism, February 26, 2010. Online, available at: https://commons.wikimedia.org/wiki/File:Clemmensen_reduction_mechanism.pngAccessed: Feb. 4, 2019.
J. Burdon, and R. C. Price, “The mechanism of the Clemmensen reduction: the substrates”, J. Chem. Soc., Chem. Comm., (12), pp. 893-894, 1986.
F. Sánchez-Viesca, M. Berros, and R. Gómez, Am. J. Chem., vol. 8(1), pp. 8-12, 2018.
J. H. White, A Reference Book of Chemistry, Section One, London, UK: University of London Press, 1960, p. 66, Hydroxonium ion.
Sh. Banigan, Ed., The Binding Force, by Scientists of the Westinghouse Research Laboratories, New York, USA: Walker and Co., 1966, p. 70, The hydrated proton.
W. F. Luder, and S. Zuffanti, The Electronic Theory of Acids and Bases, 2nd. ed., New York, USA: Dover, 1961, pp. 71-72.
F. Sánchez-Viesca, and R. Gómez, “On the Baeyer-Emmerling synthesis of indigo”, World J. Org. Chem., vol. 6(1), pp. 6-12, 2018.
F. Sánchez-Viesca, and R. Gómez, “On the mechanism of indirubin formation in the Baeyer-Emmerling synthesis”, Am. J. Chem., vol. 8(4), pp. 85-89, 2018.
S. P. Williams, M. O. Nowicki, F. Liu, R. Press, J. Goldlewski, and M. Abdel-Rasoul, “Indirubins decrease glioma invasion by blocking migratory phenotypes in both the tumor and stromal endothelial cell compartments”, Cancer Res2011; DOI: 10.1158/0008-5472.CAN-10-3026
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 Letters, No. 6, pp. 489-493, 1967.
F. Sánchez-Viesca, and R. Gómez, “On the regiochemistry in the Heyns rearrangement”, Am. J. Chem., vol. 5(3), pp. 86-89, 2015.
F. Sánchez-Viesca, and R. Gómez, “Reactivities Involved in the Regioselectivity of Osazone Formation”, World J. Org. Chem., vol. 5(1), pp. 11-16, 2017.
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.
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.
Z. Rappoport, Ed., Handbook of Tables for Organic Compound Identification, 3rd. ed., Cleveland, USA: Chemical Rubber, 1967, pp. 436-437.
F. Sánchez-Viesca, and R. Gómez, “On the mechanism of the Froehde reaction”, World J. Org. Chem., vol. 7(1), pp. 1-4, 2019.