Diethoxytriphenylphosphorane: a mild, regioselective cyclodehydrating reagent for conversion of diols to cyclic ethers: stereochemistry, synthetic utility, and scope

PL Robinson, CN Barry, JW Kelly…

Index: Robinson, Philip L.; Barry, Carey N.; Kelly, Jeffery W.; Evans, Slayton A. Journal of the American Chemical Society, 1985 , vol. 107, # 18 p. 5210 - 5219

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Citation Number: 57

Abstract

Abstract: Diethoxytriphenylphosphorane, Ph, P (OEt),, prepared by reaction of triphenylphosphine and diethyl peroxide, is a “hydrolytically active” dioxyphosphorane which promotes mild cyclodehydration (40-1 10 “C) of diols to cyclic ethers in neutral media. The regioselectivity in the closure of (S)-(+)-propane-1, 2-diol and@)-(-)-pentane-1, 4-diol with Ph, P (OEt), is high (8 1-82%) while the cyclodehydration of (S)-(+)-phenylethane-1, 2 ...