Studies of Cathodically-Promoted Addition Reactions of Nitromethane with Various Aldehydes
Addition of nitromethane to five heterocyclic aldehydes, anthracene-9-carboxaldehyde and ferrocenecarboxaldehyde has been studied. In all cases, the corresponding nitroalcohols are formed initially and, for the less basic aldehydes, this product can be isolated in good to excellent yield. For the more basic heterocyclic aldehydes, the initially formed nitroalcohol dehydrates under the reaction conditions forming the nitroolefin. This is particularly evident for the reaction of N-methylpyrrole-2-carboxaldehyde where the nitroolefin was found to add a second molecule of nitromethane forming 2-(N-methyl-2-pyrrolyl)-1,3-dinitropropane. Similar results were obtained with ferrocenecarboxaldehyde where it was possible to obtain the 1,3-dinitro compound as the sole product.
KeywordsCarbonyl Compound Excellent Yield Nitro Compound Michael Addition Nitro Nate
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