Journal of the Brazilian Chemical Society
On-line version ISSN 1678-4790
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 1678-4790. 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.