THE CHEMISTRY OF α, ω-MERCAPTOALCOHOLS IN THE PRESENCE OF DIETHOXYTRIPHENYLPHOSPHORANE. TEMPERATURE DEPENDENCE OF CYCLODEHYDRATIONS AND S-ETHYLATIONS

Philip L. Robinson Laboratories of Chemistry, The University of North Carolina, Chapel Hill, North Carolina, 27514, U.S.A.

Jeffery W. Kelly Laboratories of Chemistry, The University of North Carolina, Chapel Hill, North Carolina, 27514, U.S.A.

Slayton A. Evans Jr. Laboratories of Chemistry, The University of North Carolina, Chapel Hill, North Carolina, 27514, U.S.A.

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.

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THE CHEMISTRY OF α, ω-MERCAPTOALCOHOLS IN THE PRESENCE OF DIETHOXYTRIPHENYLPHOSPHORANE. TEMPERATURE DEPENDENCE OF CYCLODEHYDRATIONS AND S-ETHYLATIONS

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THE CHEMISTRY OF α, ω-MERCAPTOALCOHOLS IN THE PRESENCE OF DIETHOXYTRIPHENYLPHOSPHORANE. TEMPERATURE DEPENDENCE OF CYCLODEHYDRATIONS AND S-ETHYLATIONS

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