Abstract
Electrochemical oxidation of catechols (1a-c) has been studied in the
presence of methyl acetoacetate (2a) and ethyl acetoacetate (2b) as
nucleophiles in aqueous solution using cyclic voltammetry and
controlled-potential coulometry. The results indicate that the quinones
derived from catechols (1a-c) participate in Michael addition reactions
with 2a and 2b to form the corresponding benzofuran derivatives (3a-f).
The electrochemical synthesis of 3a-f has been successfully performed in
an undivided cell in good yield and purity. The oxidation mechanism was
deduced from voltammetric data and by coulometry at controlled
potential. The products have been characterized after purification by
IR, H-1 NMR, C-13 NMR, MS, and single crystal X-ray diffraction. (C)
2007 Elsevier Ltd. All rights reserved.
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