Horner-Wadsworth-Emmons Reactions in THF: Effect of Hydroperoxide Species

Abstract

Horner-Wadsworth-Emmons (HWE) reactions routinely employ tetrahydrofuran (THF) as the reaction solvent. In this paper we show that THF adducts (derived from THF-hydroperoxide species) of HWE phosphonate ester compounds are formed under microwave irradiation (i.e., under pressure), or in the presence of a reductant [e.g., P(OEt) 3 ] in a conventionally heated reaction.