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Chlorodiisopropylphosphine

Chlorodiisopropylphosphine is an organophosphorus compound with the formula [(CH<sub>3</sub>)<sub>2</sub>CH]<sub>2</sub>PCl. It is a colorless liquid that reacts with water and oxygen. The compound is used to prepare tertiary phosphines and phosphinite ligands.

Synthesis and reactions

The compound is prepared by treating phosphorus trichloride with the Grignard reagent isopropylmagnesium chloride:

PCl<sub>3</sub> + 2 (CH<sub>3</sub>)<sub>2</sub>CHMgCl → [(CH<sub>3</sub>)<sub>2</sub>CH]<sub>2</sub>PCl + 2 MgCl<sub>2</sub>

Relative to the reaction of less hindered Grignard reagents with PCl<sub>3</sub>, this reaction affords a superior yield of the monochloro derivative.

Chlorodiisopropylphosphine reacts with Grignard reagents and organolithium compounds to give phosphines:

[(CH<sub>3</sub>)<sub>2</sub>CH]<sub>2</sub>PCl + RM → [(CH<sub>3</sub>)<sub>2</sub>CH]<sub>2</sub>PR + MCl

Chlorodiisopropylphosphine reacts with alcohols and phenols to give phosphinites, this reaction typically is conducted in the presence of a base:

[(CH<sub>3</sub>)<sub>2</sub>CH]<sub>2</sub>PCl + ROH → [(CH<sub>3</sub>)<sub>2</sub>CH]<sub>2</sub>POR + HCl

Phosphinites are versatile ligands.

References