An unusual behaviour of N-(tert-butoxycarbonyl)- and N-pivaloyl-(methylthio)anilines in metallation reactions |
| |
Authors: | Maria Grazia CabidduSalvatore Cabiddu Enzo CadoniStefania De Montis Claudia FattuoniStefana Melis |
| |
Institution: | Dipartimento di Scienze Chimiche, Cittadella Universitaria di Monserrato, S.S. 554 Bivio per Sestu, I-09042 Monserrato (CA), Italy |
| |
Abstract: | The metallation reaction of N-Boc-and N-Piv-(methylthio)anilines are here described. The results show that N-Boc derivatives are metallated only by superbases to give products substituted at the thiomethylic group. N-Piv derivatives show a different behaviour: ortho-derivative is metallated by both butyllithium and superbase at the thiomethylic carbon atom, while para-derivative is metallated in ortho to the N-Piv group by butyllithium and at the thiomethylic carbon atom by superbase. The meta-derivative is metallated only by superbase at the thiomethylic carbon atom. |
| |
Keywords: | metallation lithiation thioethers anilines |
本文献已被 ScienceDirect 等数据库收录! |