Electrochemical bromochlorination of peracetylated glycals |
| |
Authors: | Damljanović Ivan Stevanović Dragana Vukićević Mirjana Vukićević Rastko D |
| |
Institution: | aDepartment of Chemistry, Faculty of Science, University of Kragujevac, R. Domnovi?a 12, 34000 Kragujevac, Serbia;bDepartment of Pharmacy, Faculty of Medicine, University of Kragujevac, S. Markovi?a 69, 34000 Kragujevac, Serbia |
| |
Abstract: | Peracetylated glycals—3,4,5-tri-O-acetyl-d-glucal (1a), 3,4,5-tri-O-acetyl-d-galactal (1b) and 3,4-di-O-acetyl-6-deoxy-l-glucal (1c)—have been bromochlorinated by a suitable halogenating agent, generated electrochemically from a mixture of bromides and chlorides in dichloromethane. The reaction was performed in two ways: (i) by a constant current electrolysis (2 F mol−1) of bromides and substrates in a milieu containing an excess of chlorides (Br?/1/Cl? = 1:1:6.8) and (ii) by anodic generation of free chlorine from chlorides (2 F mol−1) and subsequent addition of bromides and substrates in a ratio Br?/1 = 1:1. The corresponding 2-bromo-2-deoxy-glycopyranosyl chlorides were obtained in high yields. |
| |
Keywords: | Peracetylated glycals Bromochlorination Electrochemical halogenation Cyclic voltammetry 2-Bromoglycopyranosyl chlorides |
本文献已被 ScienceDirect PubMed 等数据库收录! |
|