1,3-Butadiene → 1,1,5-Trichloro-pent-3-ene-1-phosphonic dichloride

Participants

Reaction Steps

11.8 g (0.05 mole) trichloromethane phosphonic dichloride was dissolved in 10 ml dry methylene chloride, cooled, and a cold solution of 4 g butadiene in 10 ml methylene chloride, which also contained 134 mg (1 mmole) anhydrous cupric chloride and 206 mg (1.5 mmole) triethylammonium chloride, was added. The resulting homogeneous solution was heated in the absence of air, in a sealed ampoule, at 100° for 8 hours. After cooling, the reaction product was freed from solvent, and fractionated through a short Vigreux column. 9.6 g pure 1:1 adduct, 1,1,5-trichloro-pent-3-ene-1-phosphonic dichloride was obtained, bp/0.05: 92°-93°. Found: Cl: 61.3%, Calc. for C5H6Cl5OP: 61.0%.

Provenance & Evidence