Reactions of Fluoronitrobenzenes with TBD in Acetonitrile in the Presence of Water Molecules

Products of the reaction between three fluorinated nitrobenzenes (2,3,4,6-tetrafluoronitrobenzene, mNF4; 2,3,4,5-tetrafluoronitrobenzene, oNF4; pentafluoronitro-benzene, NF5) and 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) in the presence of the water molecules in acetonitrile were isolated and identified by analytical and spectroscopic methods. The reaction products included ortho and para substituted nitro-compounds. The kinetics of these reactions is independent of the substrates studied. The rate-determining step of these reactions is the hydrolysis of one ring of the TBD molecule after the fast formation of the Meisenheimer complex. The mechanism of these reactions and the structures of the products are discussed.