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Theoretical studies on cycloaddition reactions

Journal of Cheminformatics20146 (Suppl 1) :P2

  • Published:


  • Nitrile
  • Methacrylate
  • Acrylate
  • Oxime
  • Lewis Acid

Cycloaddition reactions represent one of the most powerful processes in organic chemistry. The most common types of cycloaddition reactions are the Diels-Alder (DA) and the 1,3-dipolar cycloaddition reactions (1,3-DCs) which lead to five and six membered rings, respectively.

In our ongoing efforts to contribute to the understanding of DA and 1,3-DCs; we studied the following using the B3LYP/6-31G(d) level of theory:

1. The 1,3-DCs of the pyridinium-3-olates and pyrazinium-3-olates with methyl acrylate and methyl methacrylate [1, 2].

2. The competitive hetero-DA and 1,3-DCs of methyl glyoxylate oxime and its tautomeric nitrone with cyclopentadiene in the absence and in the presence of BF3 as a Lewis acid catalyst [3].

3. A systematic study on the 1,3-DCs of C60 with substituted nitrile oxides (RCNO; R = F, Cl, Br, NC, CN and NO2) [4].

Among the outcomes of our investigations is the successful use of theoretical methods to understand the regio- and stereoselectivity of the reactions considered. It is expected that experimentalists find the results useful for synthesis involving these moieties and cycloaddition reactions. This presentation will overview our ongoing research program to have more understanding of these cycloaddition reactions.

Authors’ Affiliations

Computational Chemistry Group, Department of Chemistry, Faculty of Science, University of Mauritius, Réduit, Mauritius
Departamento de Química Orgánica, Universidad de Valencia, Dr. Moliner 50, 46100 Burjassot, Valencia, Spain


  1. Rhyman L, Abdallah HH, Jhaumeer-Laulloo S, Domingo LR, Joule JA, Ramasami P: The 1,3-Dipolar Cycloaddition of 1H-pyridinium-3-olate and 1-Methylpyridinium-3-olate with Methyl Acrylate: A Density Functional Theory Study. Tetrahedron. 2010, 66: 9187-9193. 10.1016/j.tet.2010.09.071.View ArticleGoogle Scholar
  2. Domingo LR, Sáez JA, Joule JA, Rhyman L, Ramasami P: A DFT Study of the [3+2] versus [4+2] Cycloaddition Reactions of 1,5,6-Trimethylpyrazinium-3-olate with Methyl Methacrylate. J Org Chem. 2013, 78: 1621-1629. 10.1021/jo302730q.View ArticleGoogle Scholar
  3. Rhyman L, Ramasami P, Joule JA, Sáez JA, Domingo LR: A DFT Study of the Regio- and Stereoselectivity of the 1,3-Dipolar Cycloaddition of C-Methyl Substituted Pyrazinium-3-olates with Methyl Acrylate and Methyl Methacrylate. RSC Adv. 2013, 3: 447-457. 10.1039/c2ra22332e.View ArticleGoogle Scholar
  4. Rhyman L, Jhaumeer-Laulloo S, Domingo LR, Joule JA, Ramasami P: Computational Assessment of 1,3-Dipolar Cycloaddition of nitrile oxides with ethene and [60]fullerene. Heterocycles. 2012, 84: 719-735. 10.3987/COM-11-S(P)46.View ArticleGoogle Scholar


© Rhyman et al; licensee Chemistry Central Ltd. 2014

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