Transformation of homoallylic alcohol oxides into 3-hydroxytetrahydrofurans in aqueous HClO4

MV Chirskaya, AA Vasil'ev, SV Shorshnev…

Index: Chirskaya; Vasil'ev; Shorshnev; Sviridov Russian Chemical Bulletin, 2006 , vol. 55, # 7 p. 1300 - 1303

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Citation Number: 3

Abstract

Abstract Hydrolysis of allyl carbinol oxides in aqueous HClO 4 gave the corresponding 1, 2, 4-triols. On heating in the same reaction medium, they underwent cyclization into 3- hydroxytetrahydrofurans. The method is restricted to substrates that can generate stable carbocations via elimination of the hydroxy group from position 4 in intermediate 1, 2, 4- triols.