Cyclodehydration and Chlorination of Simple Diols with Triphenylphosphine and tert-Butyl Hypochlorite

Article abstract of DOI:10.1021/jo00165a008

The reagent triphenylphosphine-tert-butyl hypochlorite converts 1,4-diols into the corresponding tetrahydrofurans and 1,2-diols into a mixture of the regioisomeric chlorohydrins and the epoxides at -78 deg C followed by warming to ambient temperature (ca. 30 deg C).Symmetrical diols give largely chlorohydrins and dichlorides.