The low temperature reaction of diazomethane with 1,3,5‐trinitrobenzene: Nucleophilic aromatic addition VIII

Abstract

AbstractThere is a strong temperature effect on the reaction of 1,3,5‐trinitrobenzene with diazomethane. At 0° three methylene groups are introduced and the product is the trinitro derivative I (found earlier).Below −80°, again three methylene groups are introduced, but the main product is a dinitro compound II, isomeric with I but with strikingly different properties.The methylene groups in II are incorporated in a seven‐membered ring, a cyclopropane ring and an isoxazoline ring, the latter arising by an unusual participation of one of the nitro groups.The structural proof of II rests on spectroscopic evidence and specific chemical reactions.