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What Controls Regiochemistry in 1,3-Dipolar Cycloadditions of Münchnones with Nitrostyrenes?

descriptionPublicationkeyboard_double_arrow_right Article 27 Sep 2013 English Publisher:American Chemical Society (ACS)Journal:Organic Letters, volume 15, pages 5,218-5,221 (issn: 1523-7060, eissn: 1523-7052, Copyright policy )
Authors: Gordon W. Gribble; Russell P. Hughes; Justin M. Lopchuk;

doi: 10.1021/ol402385v

pmid: 24073889

What Controls Regiochemistry in 1,3-Dipolar Cycloadditions of Münchnones with Nitrostyrenes?

Abstract

The distinct experimentally observed regiochemistries of the reactions between mesoionic münchnones and β-nitrostyrenes or phenylacetylene are shown by DFT/BDA/ETS-NOCV analyses of the transition states to be dominated by steric and reactant reorganization factors, rather than the orbital overlap considerations predicted by Frontier Molecular Orbital (FMO) Theory.

Related Organizations
Keywords

Molecular Structure, Cyclization, Quantum Theory, Pyrroles, Stereoisomerism, Oxazoles, Styrenes

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citations
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
52
Top 10%
Top 10%
Top 10%
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