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Regioselective cleavage reaction of the methylenedioxy ring in aromatic compounds containing electron withdrawing groups with sodium alkoxides alcohols in dmso

Regioselective cleavage reaction of the methylenedioxy ring in aromatic compounds containing electron withdrawing groups with sodium alkoxides alcohols in dmso

Heterocycles 31(6): 1067-1076

The reaction of 6-bromopiperonal (1) with sodium alkoxides (MeONa or PhCH2ONa)-alcohols (MeOH or PhCH2OH), and sodium alkoxides (MeONa, PhCH2ONa or PhONa)-phenol (PhOH) in dimethyl sulfoxide gave 3-hydroxybenzene derivatives (3, 5 and 6) and 4-hydroxybenzene derivative (4), respectively. The reactivity and formational mechanism of various nucleophilic reagents (alkoxide anions) formed from the alcohols and phenol by sodium alkoxides in the regioselective cleavage reactions are discussed.

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