Alkylatlon orientation rules in conjugate addition of grignard reagents to nitropyrrole and nitrothiophene systems |
| |
| Institution: | 1. Dipartimento Scienze Chimiche, Università, via S. Agostino 1, 62032 Camerino (McItaly;2. Dipartimento Chimica Organica, Università, viale Risorgimento 4, 40136 BolognaItaly;1. Nanosystem Research Institute, National Institute of Advanced Industrial Science and Technology, 1-2-1 Namiki, Tsukuba, Ibaraki 305-8564, Japan;2. Toda R&D Center, Tokyo Chemical Industry Co., Ltd., 12-8 Kita-cho, Sasame, Toda City, Saitama 335-0033, Japan;1. Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, Key Laboratory of Cluster Science of Ministry of Education, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, 5 South Zhongguancun Street, Beijing, 100081, China;2. Heeger Beijing Research and Development Center School of Chemistry, Beihang University, Beijing, 100191, China;1. College of Chemistry, Biology and Material Engineering, Suzhou University of Science and Technology, 1 Ke Rui Road, Suzhou, Jiangsu, 215009, PR China;2. Printable Electronics Research Center, Suzhou Institute of Nano-Tech and Nano-Bionics (SINANO), Chinese Academy of Sciences, 398 Ruo Shui Road, SEID SIP, Suzhou, Jiangsu, 215123, PR China;3. Department of Chemistry, Shanghai Key Laboratory of Green Chemistry and Chemical, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, PR China;4. Department of Chemistry, Xi''an Jiaotong Liverpool University, 111 Ren Ai Road, Dushu Lake Higher Education Town, Suzhou, Jiangsu, 215123, PR China;1. School of Mathematics and Statics, North China University of Water Resources and Electric Power, Zhengzhou 450046, China;2. Basic Teaching Department, Jiaozuo University, Jiaozuo 454000, China;3. State Key Laboratory of Molecular Reaction Dynamics, Theoretical and Computational Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China |
| |
| Abstract: | Conjugate addition of various Grignard reagents to 1-alkyl-2-nitropyrroles and to 2-nitrothiophene has been investigated. 1-Alkyl-2-nitropyrroles undergo alkylation at 3 and 5 positions with prevalence of the latter isomer. On the contrary, in 2-nitrothiophene system, formation of the 3-isomer prevails. In both systems, a bulkier Grignard reagent favours the 5-isomer formation. This trend can be reversed increasing steric hindrance exerted by the 1-substituent of 2-nitropyrrole. 1-(Tri-isopropylsilyl)-3-nitropyrrole and 3-nitrothiophene give exclusively the 2-isomer. This rection allows 2-alkyl-3-nitrothiophenes and pyrroles to be synthesized with a one-pot procedure instead of the classical multi-stage reaction. |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
