Iodide reagent controlled reaction pathway of iodoperoxidation of alkenes: a high regioselectivity synthesis of α- and β-iodoperoxidates under solvent-free conditions
| Autor: | Qun Cai, Chen Hongxiang, Chen Cheng, Gao Xiaofang, Hongling Yang, Fang Gao, Qi Jia, Chuangjian Wang |
|---|---|
| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Markovnikov's rule Iodide Cationic polymerization Regioselectivity chemistry.chemical_element 010402 general chemistry Iodine 01 natural sciences Pollution Combinatorial chemistry Ammonium iodide 0104 chemical sciences Adduct chemistry.chemical_compound chemistry Reagent Environmental Chemistry |
| Zdroj: | Green Chemistry. 20:2225-2230 |
| ISSN: | 1463-9270 1463-9262 |
| Popis: | A highly atom economical, efficient and environmentally friendly iodoperoxidation of alkenes with tert-butyl hydroperoxide (TBHP) and iodide/iodine is reported in this paper. This method afforded a convenient path to obtain two different configurations of iodoperoxidates from the same starting materials. Notably, the regiodivergent iodoperoxidation reaction was achieved by using different iodide reagents. A series of control experiments were performed, which suggested the involvement of a radical pathway for the anti-Markovnikov type iodoperoxidates (α) in the combination of ammonium iodide (NH4I)/TBHP, and an active cationic iodine pathway for the Markovnikov type adduct (β) with iodine (I2) and TBHP. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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