The remarkable effect of 7-amino substituents on the reactivity of 4-nitrobenzofurazans with nucleophiles
| dc.contributor.author | Crampton, M.R. | |
| dc.contributor.author | Isanbor, C. | |
| dc.contributor.author | Willett, T.C. | |
| dc.date.accessioned | 2019-08-26T17:17:26Z | |
| dc.date.available | 2019-08-26T17:17:26Z | |
| dc.date.issued | 2005 | |
| dc.description.abstract | The reactions of four 4-nitrobenzofurazans (4a–4d) substituted at the 7 position with (a) N-ethyl, (b) Nbutyl, (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 stabilization of the parent molecules 4a–4d by conjugative interaction between the 4 and 7 substituents. In alkaline solution, 4a and 4b yield the conjugate bases while 4c and 4d suffer nucleophilic substitution to give 7-hydroxy-4- nitrobenzofurazan. Reactivity here is relatively high because of the iminium ion character of the substrates. | en_US |
| dc.identifier.citation | Crampton, M. R., Isanbor, C., & Willett, T. C. (2005). The remarkable effect of 7-amino substituents on the reactivity of 4-nitrobenzofurazans with nucleophiles. Canadian journal of chemistry, 83(9), 1222-1227. | en_US |
| dc.identifier.uri | https://ir.unilag.edu.ng/handle/123456789/4786 | |
| dc.language.iso | en | en_US |
| dc.publisher | NRC Research Press | en_US |
| dc.subject | Research Subject Categories::NATURAL SCIENCES::Chemistry::Physical chemistry::Spectroscopy | en_US |
| dc.subject | benzofurazans | en_US |
| dc.subject | σ adducts | en_US |
| dc.subject | nucleophilic reactivity | en_US |
| dc.subject | substitution | en_US |
| dc.title | The remarkable effect of 7-amino substituents on the reactivity of 4-nitrobenzofurazans with nucleophiles | en_US |
| dc.type | Article | en_US |