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Electrochemical bromochlorination of peracetylated glycals

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
346
Issue
17
Identifiers
DOI: 10.1016/j.carres.2011.09.016
Keywords
  • Peracetylated Glycals
  • Bromochlorination
  • Electrochemical Halogenation
  • Cyclic Voltammetry
  • 2-Bromoglycopyranosyl Chlorides
Disciplines
  • Chemistry

Abstract

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.

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