REGIOSELECTIVE CLEAVAGE REACTION OF THE METHYLENEDIOXY RING IN AROMATIC COMPOUNDS CONTAINING ELECTRONWITHDRAWING GROUPS WITH SODIUM ALKOXIDES-ALCOHOLS IN DIMETHYL SULFOXIDE

DOI: 10.3987/COM-90-5341

Source and publish data:

Heterocycles p. 1067 - 1076 (1990)

Update date:2022-08-04

Topics:

Authors:

Imakura, Yasuhiro

Okimoto, Kazuto

Gorohata, Chizuru

Kobayashi, Shigeru

Kihara, Masaru

Yamashita, Shinsuke

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Article abstract of DOI:10.3987/COM-90-5341

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.

Full text of DOI:10.3987/COM-90-5341

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