1964 年 84 巻 11 号 p. 1080-1084
Effect of substituents on the N-oxidation and deoxygenation reactions of β-substituted phenazine compounds was examined because such a substituent does not have steric hindrance on the two nitrogen atoms and only their M effect is thought to affect these reactions.
N-Oxidation of phenazine compounds having a substituent with -M effect in the β-position, under a definite, comparatively weak condition, results in the formation of 10-oxides. Deoxygenation of phenazine 5, 10-dioxides possessing a substituent with -M effect in the β-position, under a definite condition, produces 5-oxide.
These facts indicate that a substituent with -M effect in the β-position increases electron density of the nitrogen atom in the 10-position of the phenazine ring and that the N-O bond in 5-position is stronger than that in the 10-position in phenazine 5, 10-dioxide.