Gas-phase reactions of benzene and derivatives triggered by hydrazine/ozone; hydroxylation vs. degradation

The reactions of benzene derivatives C6H5X (X = H, Cl, CH3 and CF3) with hydrazine and ozone in the dark (a source of OH radicals) have been studied in a flow reactor at ambient temperature. (Substituted) phenols were formed, but these were relatively unimportant compared to N-heterocyclic compounds (condensation products of cis-butenedial and analogues with hydrazine) and other (degradation) products. Benzene and (trifluoromethyl)benzene follow a similar path as toluene, also with oxidative ring opening as major reactions.