What controls regiochemistry in 1,3-dipolar cycloadditions of münchnones with nitrostyrenes?
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.
Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
Justin M
JM
Lopchuk
Russell P
RP
Hughes
Gordon W
GW
Gribble
D003500:Cyclization; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D013237:Stereoisomerism; D013343:Styrenes / Q000737:chemistry*
D010080:Oxazoles; D011758:Pyrroles; D013343:Styrenes; C011955:beta-nitrostyrene