Base induced reactions of 1‐alkoxy‐ or l‐methylthio‐l‐(α‐ or β‐hydroxyalkyl)allenes. Formation of 3‐alkoxy‐ and 3‐methylthiodihydrofurans
作者： S. Hoff , L. Brandsma , J. F. Arens
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摘要: l-Alkoxy-l-(α-hydroxyalkyl)allenes R1CH=C=C(OR2)C(OH)R3R4 (Ia) have been converted with high yields into 3-alkoxy-2,5-dihydrofurans (II) using potassium tert-butoxide in dimethyl sulfoxide. Hydrolysis of II dilute sulfuric acid afforded 3-oxotetrahydrofuran derivatives III. l-(β-Hydroxyalkyl)-l-methylthioallenes R1CH=C=C(SCH3)CH2CH2OH (IVb) and the analogous oxygen compounds IVa yielded 2-alkyl-3-methylthio-4,5-dihydrofurans (Vb) a mixture 3-methoxy-2-methyl-4,5-dihydrofurans (Va) 3-methoxy-2-methylenetetrahydrofuran VI, respectively. The preparation hydroxyallenes is described.
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