Methods: PHEPSI was synthesized by heating solution of 4-vinyl-1-cyclohexene-1,2-epoxide, methylphenylsilane, toluene, and Wilkinson's catalyst to 100°C for 24h. Column chromatography was used (silica gel; solvent, 90:10 hexane:ethyl acetate) to isolate PHEPSI. CYGEP was synthesized by refluxing solution of 4-vinyl-1-cyclohexene-1,2-epoxide, 2,4,6,8-tetramethylcyclotetrasiloxane, and toluene with a Dean-Stark trap for 2h, then cooled (5-9°C). After Lamoreaux's catalyst3 (1 drop) was added, resulting mixture was allowed to warm to room temperature (17h). Column chromatography (silica gel; solvent gradient,hexanes,90:10,80:20,ethyl acetate) was used to isolate CYGEP. Extent of reaction monitored by IR spectroscopy for disappearance of Si-H peaks for PHEPSI and CYGEP (2160 and 2100cm-1), respectively. Excess ethyl acetate removed via vacuum for both monomers. Results: Disappearance of Si-H peaks indicated completion of reactions. After purification, PHEPSI isolated in average yield (41%) as confirmed by 1H-and 13C-NMR spectroscopy. Addition of the catalyst to the resulting mixture below 5°C resulted in polymerization of solution to a gel, due to the freezing of toluene and temps above 9°C due to activation of the catalyst. After purification, CYGEP was isolated in average yield (61%) as confirmed by NMR spectroscopy. Conclusion: Two silorane monomers of interest were reproducably synthesized using modified procedures. This work was supported in part by NIH/NIDCR Grant R21 DE018336, NIH/NIDCR T32 (DE07294), and Missouri Life Science Research Board Grant (#13234-2007). 1. J.V. Crivello and D. Bi, J. Poly. Sci.: Part A: Poly Chem. 1994,32,683-697. 2. J.V. Crivello and J. L. Lee, J. Poly Sci.: Part A: Poly Chem. 1990,28,479-503.
3. H. F. Lamoreaux,U.S. Patent 3,220,972,1965.