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Paper | Regular issue | Vol 31, No. 6, 1990, pp.1067-1076
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5341
Regioselective Cleavage Reaction of the Methylenedioxy Ring in Aromatic Compounds Containing Electron-withdrawing Groups with Sodium Alkoxides-Alcohols in Dimethyl Sulfoxide

Yasuhiro Imakura,* Kazuto Okimoto, Chizuru Gorohata, Shigeru Kobayashi, Masaru Kihara, and Shinsuke Yamashita

*Faculty of Sciences, Naruto University of Education, Takashima, Naruto-shi, Tokushima 772- , Japan


The reaction of 6-bromopiperonal (1) with sodium alkoxides (MeONa or PhCH2ONa)-alcohols (MeOH or PhCH2OH), and sodium alkoxides (MeONa, PhCH2Na 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.