What controls regiochemistry in 1, 3-dipolar cycloadditions of munchnones with nitrostyrenes?
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JM Lopchuk, RP Hughes, GW Gribble
Organic letters, 2013
ACS Publications
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.
