THE CHEMISTRY OF α, ω-MERCAPTOALCOHOLS IN THE PRESENCE OF DIETHOXYTRIPHENYLPHOSPHORANE. TEMPERATURE DEPENDENCE OF …

PL Robinson, JW Kelly, SA Evans Jr

Index: Robinson, Philip L.; Kelly, Jeffery W.; Slayton, A. Evans Phosphorus and Sulfur and the Related Elements, 1987 , vol. 31, p. 59 - 70

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Citation Number: 9

Abstract

Abstract Diethoxytriphenylphosphorane (DTPP) is easily prepared by oxidative addition of triphenylphosphine with diethyl peroxide. DTPP converts a variety of mercaptoalcohols to cyclic sulfides as well as hydroxythioethers. The temperature dependence (+ 25→− 25° C) of the product distribution has synthetic potential.

~51%

~35%

~71%

~51%

~90%

~17%

~18%

~62%

~28%

Synthesis of 2-alkyl (aryl) thietanes

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Dioxyphosphoranes, an Emerging Class of Versatile Reagents f...

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[Bordwell; McKellin Journal of the American Chemical Society, 1951 , vol. 73, p. 2251]