Allyl chloride → Trichloro(3-chloropropyl)silane

Reaction equation

[SiH:1]([Cl:4])([CH3:3])[CH3:2].[SiH:5]([Cl:8])([Cl:7])[Cl:6].[CH2:9]([Cl:12])[CH:10]=[CH2:11]>>[Si:5]([CH2:11][CH2:10][CH2:9][Cl:12])([Cl:8])([Cl:7])[Cl:6].[Si:1]([CH2:11][CH2:10][CH2:9][Cl:12])([CH3:3])([CH3:2])[Cl:4]

Participants

Reactant 3

HCID 7850Allyl chloride

HCID 24811Trichlorosilane

HCID 66108Chlorodimethylsilane

Product 2

HCID 75693Trichloro(3-chloropropyl)silaneYield 60.4%

HCID 82765Silane, chloro(3-chloropropyl)dimethyl-Yield 8.6%

Procedure

In a 100 ml apparatus, there were combined 7.1 g (0.075 mol) of Me2SiHCl, 10.2 g (0.075 mol) of Cl3SiH, and 5.7 g (0.075 mol) of allyl chloride. Pt catalyst solution (0.01 ml) was added at 33° C., causing an exothermic reaction to 47° C. in 7 min. VPC analysis 14 min. later showed a complete reaction. Vacuum distillation yielded 60.4% Cl3SiCH2CH2CH2Cl and 8.6% Me2SiClCH2CH2CH2Cl. This example shows that Me2SiHCl is an effective promoter for the reaction of Cl3SiH with allyl chloride at the equimolar level.