Conversion of (Z)-1, 4-dihydroxyalk-2-enes into 2, 5-dihydrofurans and of alkane-1, 4-diols into tetrahydrofurans via acid-catalysed cyclisation of the monoisoureas …

MG Duffy, DH Grayson

Index: Duffy, Michael G.; Grayson, David H. Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 13 p. 1555 - 1563

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Citation Number: 15

Abstract

Reaction of (Z)-1,4-dihydroxybut-2-ene 2a with the diaryldialkoxysulfane 3 has been reported 9 to give 2,5-dihydrofuran in 84% yield, but the reagent is expensive. Diethoxytriphenylphosphorane 4 efficiently cyclises the same diol 10 but this reagent must be prepared from explosive diethyl peroxide. The environmentally toxic butyltrichlorotin reacts with the diol 2a to give 2,5-dihydrofuran (88%) together with some crotonaldehyde. 11 Barry and Evans have described 12,13 ...