On the reaction of 3-bromo-2-nitrobenzo[b]thiophene with some ortho-substituted anilines: an analysis of the products of reaction and of their NMR and MS properties |
| |
| Institution: | 1. Dipartimento di Chimica Farmaceutica e Tossicologica, Università degli Studi Federico II, Via D. Montesano 49, I-80131 Napoli, Italy;2. Dipartimento di Chimica e Tecnologie Farmaceutiche, Università di Palermo, Via Archirafi 32, I-90123 Palermo, Italy;3. Dipartimento di Chimica Organica A. Mangini, Università di Bologna, Via S. Donato 15, I-40127 Bologna, Italy;1. School of Materials Science and Engineering, Guangdong Provincial Key Laboratory of Advanced Energy Storage Materials, South China University of Technology, Guangzhou, 510641, People''s Republic of China;2. Key Laboratory for Fuel Cell Technology in Guangdong Province, Guangzhou, 510641, People''s Republic of China;3. China-Australia Joint Laboratory for Energy & Environmental Materials, Griffith University, Nathan, QLD 4111, Australia |
| |
| Abstract: | The title reaction, carried out in DMF in the presence of triethylamine or potassium carbonate, has furnished the ‘expected’ 3-amino-2-nitrobenzob]thiophenes 2o together with the ‘unexpected’ 2-amino-3-nitrobenzob]thiophenes 3o, thus recalling the situation observed with other weak nucleophiles in the presence of non-nucleophilic bases. The effects (electronic as well as steric) of the ortho-substituent (OH, NH2, OMe, Me, Et, F, Cl and Br) on the course of the reaction have been investigated, determining their influence on yields and product ratios (2o/3o). An analysis of 13C NMR and MS spectra of 2o and 3o has been carried out. Ab initio computations on 2of, 2oi, 3of and 3oi at DFT level have furnished informations on their geometry and stability in the gas phase, thus allowing to assign a role to their stability on the course of the reaction as well as on some EI-MS results. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
