Dichlorotriphenylphosphorane

Dichlorotriphenylphosphorane may be used in the synthesis of the following:

• tertiary benzanilide derivatives
• N-phosphodipeptides
• dialkyl phosphorochloridites based on the reaction of trialkyl phosphites
• naphthalene ring-based calix[3]amide, via reaction with 6-amino-2-naphthoic acid
• C_2v-symmetrical cyclic tetramers of aromatic amides

Dichlorotriphenylphosphorane (Triphenylphosphine dichloride, PPh₃Cl₂) is a phosphorous halide. Stability and reactivity of dichlorotriphenylphosphorane have been studied by solid state ³¹P NMR spectroscopy. It participates in the conversion of carboxylic esters to acid halides and mechanism of this cleavage has been investigated. Modified method has been proposed in which dichlorotriphenylphosphorane participates in the synthesis of tertiary amides.

In a 100 ml four-necked flask 8 g of triphenylphosphine oxide and 25 ml of toluene were added with stirring to dissolve completely, a small amount of triethylamine catalyst was added, and then 15 ml of toluene solution containing 3.0 g of triphenylphosphine gas was slowly added dropwise for half an hour at 20 C and then stirring was continued for 8 hours, giving a molar yield of 82.2%.