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Chemistry of ketene acetals II. A simple route to 2,2-dialkoxytetrahydrofurans, γ-butyrolactones, 2-(5H)-furanones and 2-alkoxy-4,5-dihydrofurans

✍ Scribed by J.W. Scheeren; F.J.M. Dahmen; C.G. Bakker

Book ID: 104237869
Publisher: Elsevier Science
Year: 1979
Tongue: French
Weight: 216 KB
Volume: 20
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)86454-6

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✦ Synopsis

2,2-Dialkoxytetrahydrofurans 2 (a,b) have been synthesized from epoxides 1 and ketene acetals 2 using ZnC12 as a catalyst. By simple reactions compounds 2 were converted into y-butyrolactones 2, 2-(5H)-furanones 1 and 2-alkoxy-4,5_dihydrofurans g. Recently simple, cyclic orthoesters (3; R = R1 = R2 = H) have been applied successfully in syntheses of biologically active compounds. Stereoselective Claisen rearrangements via such orthoesters (R3 = allylic) gave useful inter-

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