Vinyltriethoxysilane → Phosphonic acid, P-(2-(triethoxysilyl)ethyl)-, diethyl ester
Reaction equation
[P:1]([O-:8])([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[CH:9]([Si:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])=[CH2:10]>>[Si:11]([CH2:9][CH2:10][P:1]([O:5][CH2:6][CH3:7])([O:2][CH2:3][CH3:4])=[O:8])([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14]Participants
3
Procedure
Compounds of Formula II can be synthesised via a free radical promoted addition of a dialkyl phosphite to vinyl trialkoxy silane and then distillation, according to the procedure of G. H. Barnes and M. P. David in J. Org. Chem., 25, 1191, (1960). In this paper Barnes and David reported the synthesis of a number of organosilicon phosphonate esters and acids. They utilised known procedures for the free radical addition of dialkyl phosphites to double bonds. The state of this art is described in Org. Reactions. Vol. 13, 218–222. They reacted diethyl phosphite with vinyl triethoxy silane at 120–130° C. in the presence of a free radical initiator. The desired product, (EtO)3SiCH2CH2PO(OEt)2, was obtained after careful distillation in 33% yield.