Journal of Organic Chemistry p. 6656 - 6670 (2017)
Update date:2022-08-03
Topics:
Cowie, Thomas Y.
Veguillas, Marcos
Rae, Robert L.
Rougé, Mathilde
Zurek, Justyna M.
Prentice, Andrew W.
Paterson, Martin J.
Bebbington, Magnus W. P.
Nitrofurans undergo intramolecular Diels-Alder reactions with tethered electron-poor dienophiles more rapidly and in higher yield than non-nitrated furans. Computational studies indicate that increased stabilization of a partial positive charge on the nitro-substituted carbon in both transition state and product is the driving force for these reactions. Frontier molecular orbital energy differences indicate a switch from normal to inverse electron demand upon nitration. There does not appear to be a contribution from any differences in aromatic stabilization energy between furans and nitrofurans. Calculations show that the nitrofuran reactions proceed via a highly asynchronous transition state allowing easier bond formation between two sterically hindered carbons.
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