Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 13, Pages 6656-6670Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00781
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Funding
- Leverhulme Trust [RPG-2016-008]
- European Research Council [ERG-SG/258990]
- EPSRC [EP/P001459/1]
- Heriot-Watt University
- EPSRC [EP/P001459/1, EP/J006602/1] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [1638823, EP/P001459/1, EP/J006602/1] Funding Source: researchfish
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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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