Reaction #816396

Reaction equation

4-bromostyrene

magnesium

phenylbutadiyne

chlorodiphenylphosphine

→

(4-vinylphenyl)diphenylphosphine

Solvents

THF

THF

THF

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   OtherAfter removing the solvent
4. 4
   workup.DISTILLATIONby distillation under reduced pressure
5. 5
   Otherthe residue was purified by silica gel column chromatography
6. 6
   Otherrecrystallized from a hexane solution

Procedure

Polymerizable Gold Complex (3-1) was synthesized by reacting the gold complex obtained by the reaction between sodium tetrachloroaurate (III) and triphenylphosphine having a polymerizable functional group, with phenylbutadiyne synthesized by a known method (see, P. Cadiot and W. Chodkiewicz, Chemistry of Acetylenes, H. G. Viehe, ed., Marcel Dekker, New York (1969)). More specifically, 20 ml of dried THF was added to 341 mg (14 mmol) of magnesium and thereto, a 10 ml THF solution containing 2.70 g (15 mmol) of 4-bromostyrene was added dropwise to prepare a Grignard reagent. To the resulting solution, a 10 ml THF solution containing 2.50 g (11 mmol) of chlorodiphenylphosphine was added dropwise and stirred at room temperature of 1.5 hours. After removing the solvent by distillation under reduced pressure, the residue was purified by silica gel column chromatography and recrystallized from a hexane solution to obtain 2.30 g (8.3 mmol) of (4-vinylphenyl)diphenylphosphine Compound (B).

Source