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Introducing topology to assess the synchronicity of organic reactions. Dual reactivity of oximes with alkenes as a case study

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Abstract

The synchronicity of organic reactions not always can be determined by only the analysis of transition structures. We present a case study that illustrates that topological analyses provide information regarding synchronicity that, often, is not reflected in the geometry of transition structures. We have chosen the competitive reactions of oximes with alkenes, (3 + 2) dipolar cycloaddition and ene-like reaction, which have been computationally studied to determine the parameters favoring each process. The competition between the two reactions is particularly evidenced in alkenyl oximes leading to intramolecular processes. Up to 26 examples of intramolecular reactions have been calculated and the results predicted the favored process.

Graphical abstract: Introducing topology to assess the synchronicity of organic reactions. Dual reactivity of oximes with alkenes as a case study

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Publication details

The article was received on 24 Mar 2017, accepted on 08 May 2017 and first published on 09 May 2017


Article type: Research Article
DOI: 10.1039/C7QO00233E
Citation: Org. Chem. Front., 2017, Advance Article
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    Introducing topology to assess the synchronicity of organic reactions. Dual reactivity of oximes with alkenes as a case study

    P. Merino, M. A. Chiacchio, L. Legnani, I. Delso and T. Tejero, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00233E

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