Recent Advances in Several Organic Reaction Mechanisms

Francisco Sánchez-Viesca; Martha Berros; Reina Gómez

doi:doi:10.11648/j.mc.20190701.14

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Recent Advances in Several Organic Reaction Mechanisms

Francisco Sánchez-Viesca, Martha Berros, Reina Gómez

Published in Modern Chemistry (Volume 7, Issue 1)

Received: 7 February 2019 Accepted: 18 March 2019 Published: 13 April 2019

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Abstract

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.

Published in	Modern Chemistry (Volume 7, Issue 1)
DOI	10.11648/j.mc.20190701.14
Page(s)	18-26
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), 2024. Published by Science Publishing Group

Keywords

Baeyer-Drewsen, Clemmensen Reduction, Baeyer-Emmerling, Indirubin, Regiochemistry, Internal Process, Froehde Reaction

References

[1]	Baeyer-Drewson indigo synthesis, https://en.wikipedia.org/wiki/baeyer-drewson_indigo_synthesis Accessed: Feb. 4, 2019.
[2]	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.
[3]	S. Ranganathan, “The story of indigo”, Resonance-Journal of Science Education (Bangalore, India), vol. 1(8), pp. 22-26, 1996.
[4]	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.
[5]	I. T. Millar, A shorter Sidgwick’s Organic Chemistry on Nitrogen, Oxford, UK: Clarendon, 1969, p. 322.
[6]	V. Migrdichian, Organic Synthesis, New York, USA: Reinhold, 1960, vol. 2, pp. 1631-1632.
[7]	G. Hilgetag, and A. Martini, Eds., Weygand-Hilgetag Preparative Organic Chemistry, New York, USA: Wiley, 1972, pp. 447-448.
[8]	Tomasz Dolinowski, Clemmensen reduction mechanism, February 26, 2010. Online, available at: https://commons.wikimedia.org/wiki/File:Clemmensen_reduction_mechanism.pngAccessed: Feb. 4, 2019.
[9]	J. Burdon, and R. C. Price, “The mechanism of the Clemmensen reduction: the substrates”, J. Chem. Soc., Chem. Comm., (12), pp. 893-894, 1986.
[10]	F. Sánchez-Viesca, M. Berros, and R. Gómez, Am. J. Chem., vol. 8(1), pp. 8-12, 2018.
[11]	J. H. White, A Reference Book of Chemistry, Section One, London, UK: University of London Press, 1960, p. 66, Hydroxonium ion.
[12]	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.
[13]	W. F. Luder, and S. Zuffanti, The Electronic Theory of Acids and Bases, 2nd. ed., New York, USA: Dover, 1961, pp. 71-72.
[14]	F. Sánchez-Viesca, and R. Gómez, “On the Baeyer-Emmerling synthesis of indigo”, World J. Org. Chem., vol. 6(1), pp. 6-12, 2018.
[15]	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.
[16]	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
[17]	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.
[18]	A. Hassner, and P. Catsoulacos, “On the mechanism of osazone formation”, Tetrahedron Letters, No. 6, pp. 489-493, 1967.
[19]	F. Sánchez-Viesca, and R. Gómez, “On the regiochemistry in the Heyns rearrangement”, Am. J. Chem., vol. 5(3), pp. 86-89, 2015.
[20]	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.
[21]	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.
[22]	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.
[23]	Z. Rappoport, Ed., Handbook of Tables for Organic Compound Identification, 3rd. ed., Cleveland, USA: Chemical Rubber, 1967, pp. 436-437.
[24]	F. Sánchez-Viesca, and R. Gómez, “On the mechanism of the Froehde reaction”, World J. Org. Chem., vol. 7(1), pp. 1-4, 2019.

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APA Style

Francisco Sánchez-Viesca, Martha Berros, Reina Gómez. (2019). Recent Advances in Several Organic Reaction Mechanisms. Modern Chemistry, 7(1), 18-26. https://doi.org/10.11648/j.mc.20190701.14

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ACS Style

Francisco Sánchez-Viesca; Martha Berros; Reina Gómez. Recent Advances in Several Organic Reaction Mechanisms. Mod. Chem. 2019, 7(1), 18-26. doi: 10.11648/j.mc.20190701.14

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AMA Style

Francisco Sánchez-Viesca, Martha Berros, Reina Gómez. Recent Advances in Several Organic Reaction Mechanisms. Mod Chem. 2019;7(1):18-26. doi: 10.11648/j.mc.20190701.14

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@article{10.11648/j.mc.20190701.14,
  author = {Francisco Sánchez-Viesca and Martha Berros and Reina Gómez},
  title = {Recent Advances in Several Organic Reaction Mechanisms},
  journal = {Modern Chemistry},
  volume = {7},
  number = {1},
  pages = {18-26},
  doi = {10.11648/j.mc.20190701.14},
  url = {https://doi.org/10.11648/j.mc.20190701.14},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20190701.14},
  abstract = {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.},
 year = {2019}
}

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TY  - JOUR
T1  - Recent Advances in Several Organic Reaction Mechanisms
AU  - Francisco Sánchez-Viesca
AU  - Martha Berros
AU  - Reina Gómez
Y1  - 2019/04/13
PY  - 2019
N1  - https://doi.org/10.11648/j.mc.20190701.14
DO  - 10.11648/j.mc.20190701.14
T2  - Modern Chemistry
JF  - Modern Chemistry
JO  - Modern Chemistry
SP  - 18
EP  - 26
PB  - Science Publishing Group
SN  - 2329-180X
UR  - https://doi.org/10.11648/j.mc.20190701.14
AB  - 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.
VL  - 7
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 (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

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APA Style

Francisco Sánchez-Viesca, Martha Berros, Reina Gómez. (2019). Recent Advances in Several Organic Reaction Mechanisms. Modern Chemistry, 7(1), 18-26. https://doi.org/10.11648/j.mc.20190701.14

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ACS Style

Francisco Sánchez-Viesca; Martha Berros; Reina Gómez. Recent Advances in Several Organic Reaction Mechanisms. Mod. Chem. 2019, 7(1), 18-26. doi: 10.11648/j.mc.20190701.14

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AMA Style

Francisco Sánchez-Viesca, Martha Berros, Reina Gómez. Recent Advances in Several Organic Reaction Mechanisms. Mod Chem. 2019;7(1):18-26. doi: 10.11648/j.mc.20190701.14

Copy | Download

@article{10.11648/j.mc.20190701.14,
  author = {Francisco Sánchez-Viesca and Martha Berros and Reina Gómez},
  title = {Recent Advances in Several Organic Reaction Mechanisms},
  journal = {Modern Chemistry},
  volume = {7},
  number = {1},
  pages = {18-26},
  doi = {10.11648/j.mc.20190701.14},
  url = {https://doi.org/10.11648/j.mc.20190701.14},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20190701.14},
  abstract = {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.},
 year = {2019}
}

Copy | Download

TY  - JOUR
T1  - Recent Advances in Several Organic Reaction Mechanisms
AU  - Francisco Sánchez-Viesca
AU  - Martha Berros
AU  - Reina Gómez
Y1  - 2019/04/13
PY  - 2019
N1  - https://doi.org/10.11648/j.mc.20190701.14
DO  - 10.11648/j.mc.20190701.14
T2  - Modern Chemistry
JF  - Modern Chemistry
JO  - Modern Chemistry
SP  - 18
EP  - 26
PB  - Science Publishing Group
SN  - 2329-180X
UR  - https://doi.org/10.11648/j.mc.20190701.14
AB  - 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.
VL  - 7
IS  - 1
ER  -

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