Abstract

CERECETTO, Hugo; GONZALEZ, Mercedes; LAVAGGI, M. Laura  and  PORCAL, Williams. Preparation of phenazine N⁵,N¹⁰-dioxides: Effects of benzofuroxan substituents in the outcome of their expansion reaction with phenolates. J. Braz. Chem. Soc. [online]. 2005, vol.16, n.6a, pp. 1290-1296. ISSN 0103-5053.  http://dx.doi.org/10.1590/S0103-50532005000700030.

The mesomeric effects of the benzofuroxan substituent in the preparation of phenazine N⁵,N¹⁰-dioxides are described. The electronic characteristics of the substituent in 5-substituted benzofuroxans determine the ratio of the 7- and 8-isomers of phenazine N⁵,N¹⁰-dioxides when substituted phenols are used.

Keywords : phenazine N⁵,N¹⁰-dioxide; benzofuroxan tautomerism; mesomeric effect.