Influence of a perfluorobutyl substituent on the rearrangement of prop-2-ynyl diethylphosphites to allenic phosphonates

Abstract

The Prop-2-ynyl diethylphosphites n-C₄F₉–CC-CR¹R²OP(OEt)₂ are obtained from the reaction of the corresponding prop-2-ynyl alcohols with diethyl chlorophosphite; the rearrangement of these phosphates into α-perfluorobutylallenic phosphonates is found to depend on the nature of the substituent R¹ and R², and an unexpected HF elimination is found for R¹= H, R²= Me.