Synthesis of quinoline complexes
Silyl chloride and bromide complexes are prepared quantitatively from the reaction of 2-trimethylsiloxyquinoline with the appropriate (halomethyl)dimethylchlorosilane in dry benzene.
Fluoride and triflate derivatives are obtained from reactions of the silyl chloride complex with antimony trifluoride and trimethylsilyl triflate respectively
Synthesis of model complexes
The hydrolysis of the above chloride complex readily forms the parent disiloxane D (0% substitution model).
By titration of D with aliquots of trimethylsilyl triflate, a linear relationship between the ring 13C chemical shift change and the proportion of trimethylsilyl triflate in the solution is found. After two equivalents of triflate have been added, no further significant chemical shift changes occur and the NMR data are consistent with structure E. This is the NMR model for complete substitution (100% O(donor)-Si bond)
