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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,  

 

期刊: Recueil des Travaux Chimiques des Pays‐Bas  (WILEY Available online 1969)
卷期: Volume 88, issue 5  

页码: 609-619

 

ISSN:0165-0513

 

年代: 1969

 

DOI:10.1002/recl.19690880513

 

出版商: WILEY‐VCH Verlag

 

数据来源: WILEY

 

摘要:

Abstractl‐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 potassiumtert‐butoxide in dimethyl sulfoxide. Hydrolysis of II with 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) and a mixture of 3‐methoxy‐2‐methyl‐4,5‐dihydrofurans (Va) and 3‐methoxy‐2‐methylenetetrahydrofuran VI, respectivel

 

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