121001-03-4Relevant articles and documents
Nucleophilic photosubstitutions of o-methoxynitrobenzenes
Bunce, Nigel J.,Stephenson, Karen Labonte
, p. 220 - 226 (2007/10/02)
We report a new synthesis of 3-nitroveratrole, based on the directed lithiation of veratrole, and photochemical substitutions of both 3-nitroveratrole and o-nitroanisole with several nucleophiles.Both aromatic substrates undergo photocyanation meta to the nitro group.With hydroxide ion, 3-nitroveratrole reacts meta to the nitro group, but 2-nitroanisole undergoes replacement of either substituent, the proportion of reaction at each site depending upon the OH(-) concentration. 3-Nitroveratrole undergoes an inefficient reaction with butylamine at each methoxy group; this reaction is apparently second order in amine.The reaction between o-nitroanisole and diethylamine results only in photohydrolysis.Keywords: photosubstitution, nucleophilic, 3-nitroveratrole, o-nitroanisole