Stereochemical Study on Nitro Tautomerization of Nitronate Adducts from Conjugate Addition of RMgX to a 4-Methoxy-1-nitronaphthalene System

Article abstract of DOI:10.1021/jo01301a021

Addition of RMgX to 4-methoxy-1-nitronaphthalene (1) leads to formation of nitronate 1,4 adduct (2) together with lesser amounts of 1,6 addition product (3).On treatment with aqueous acetate-acetic acid buffer, 2 is converted into a nitronate anion which