The Reaction of Hindered Phenols with Diazomethane

The reaction of 2,6-di-t-butyl-4-nitrophenol with diazomethane yields the nitronic ester exclusively, whereas 2,6-diisopropyl-4-nitrophenol reacts with diazomethane to give a mixture of the nitronic ester and the corresponding anisole. The reaction of 10-nitro-9-anthrone with diazomethane gives the monoxime of anthraquinone and formaldehyde. Silation of 2,6-di-t-butyl-4-nitrophenol with bis(trimethylsilyl)acetamide gives an unstable nitronic ester which rearranges to the trimethylsilyl ether.