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

Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
Organic Letters (Impact Factor: 6.32). 09/2013; 15(20). DOI: 10.1021/ol402385v
Source: PubMed

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.

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