The remarkable effect of 7-amino substituents on the reactivity of 4-nitrobenzofurazans with nucleophiles

MR Crampton, C Isanbor…

Index: Crampton, Michael R.; Isanbor, Chukwuemeka; Willett, Thomas C. Canadian Journal of Chemistry, 2005 , vol. 83, # 9 p. 1222 - 1227

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Citation Number: 4

Abstract

The reactions of four 4-nitrobenzofurazans (4a 4d) substituted at the 7 position with (a) N- ethyl,(b) N-butyl,(c) piperidino, or (d) pyrrolidino groups have been examined with sulfite ions and with hydroxide ions in water DMSO (80: 20, v/v). Addition of sulfite at the 5 position gives σ adducts with equilibrium constants ca. 105 lower than that for the formation of the corresponding adduct from 4-nitrobenzofurazan. These reductions are attributed to the ...