Abstract l‐Alkoxy‐l‐(α‐hydroxyalkyl)allenes R 1 CH=C=C(OR 2 )C(OH)R 3 R 4 (Ia) have been converted with high yields into 3‐alkoxy‐2,5‐dihydrofurans (II) using potassium tert ‐butoxide in dimethyl sulfoxide. Hydrolysis of II with dilute sulfuric acid afforded 3‐oxotetrahydrofuran derivatives III. l‐(β‐Hydroxyalkyl)‐l‐methylthioallenes R 1 CH=C=C(SCH 3 )CH 2 CH 2 OH (IVb) and the analogous oxygen compounds IVa yielded 2‐alkyl‐3‐methylthio‐4,5‐dihydrofurans (Vb) and a mixture of 3‐methoxy‐2‐methyl‐4,5‐dihydrofurans (Va) and 3‐methoxy‐2‐methylenetetrahydrofuran VI, respectively. The preparation of the hydroxyallenes is described.
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Hoff et al. (1969) studied this question.
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