Electroreductive generation of nitrosoarenes: application towards the nitroso Diels-Alder reaction
Caterina Campinoti1, Federico Maria Vivaldi1, Marco Lessi1,2
1Department of Chemistry and Industrial Chemistry, University of Pisa, Via Giuseppe Moruzzi, 13, 56124, Pisa, Italy. antonio.delvecchio@unipi.it.
None:
Herein, we report a simplified protocol for the electroreduction of nitroarenes, avoiding the use of stoichiometric reducing metals or sacrificial electrodes. Alternating current electrolysis enabled fine control over the selective generation of elusive nitrosoarenes, reducing dramatically the formation of side overreduction products. The developed conditions were also compatible with the nitroso Diels-Alder reaction of various cyclic dienes, allowing easy access to azabicyclo[2.2.2]octene derivatives.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Nitration of Benzene
Nitrosation of Enols
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Preparation of Nitriles
Preparation of Amines: Reduction of Oximes and Nitro Compounds
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction


