Reactions of the chloro(diisopropylamino)phosphanylium cation with unsaturated alcohols

Abstract

The chloro(diisopropylamino)phosphanylium cation [(Prⁱ₂N)(Cl)P]⁺[AlCl₄]^–1 reacts with prop-2-ynyl alcohols 2a–d to give prop-2-ynyl aminophosphonic chlorides 3a–d in good yield. Using cinnamyl alcohol and benzyl alcohol instead of 2a–d, the reactions of cation 1 afforded the corresponding aminophosphonic chlorides. In the, reaction of cation 1 with ethanol, however, no aminophosphonic chloride 8 could be isolated. The yields of these reactions were better when two equivalents of cation 1 were used. The reaction mechanisms are also discussed.