Réaction #93783

Équation de réaction

allyl chloride

Et3SiH

Cl3SiH

allyl chloride

→

Et3SiCH2CH2CH2Cl

Rendement 40.9%

Conditions de réaction

Traitement

1. 1
   Autrean exothermic reaction to 108.5° C. over 16 min
2. 2
   Températurewith heat
3. 3
   Températureat reflux (up to 114° C.) over 170 min
4. 4
   workup.DISTILLATIONVacuum distillation

Mode opératoire

In a 100 ml apparatus, there were combined 11.6 g (0.1 mol) of Et3SiH, 1.7 g (0.0125 mol) of Cl3SiH and 0.05 ml of Pt catalyst solution. The mixture was heated to 65° C. and addition of 7.7 g (0.1 mol) of allyl chloride begun. There was an exothermic reaction to 108.5° C. over 16 min, followed by a temperature drop. Addition of allyl chloride was complete in 31 min, with heat then applied at reflux (up to 114° C.) over 170 min. Vacuum distillation yielded 7.88 g (40.9%) of Et3SiCH2CH2CH2Cl with a Et3SiCH2CH2CH2Cl/Et3SiCl selectivity ratio of 1.13. This example shows that this sequence of combination of reactants allows the Cl3SiH promoter to be consumed, at which point the reaction of Et3SiH with allyl chloride proceeds at the low rate and selectivity exhibited in Comparative Example DD.

Source