We report the results from the reactions of 1-phenylethanol, 2-methylpropanol, trimethylsilanol and triphenylsilanol with TEMPO, OH-TEMPO and Br-TEMPO salt at different reaction conditions to obtain model functionalized compounds. With 1-phenylethanol, the ketone compound was obtained as expected, but when using triphenylsilanol the corresponding hexaphenyldisiloxane [di(triphenylsilane)ether] was obtained in crystal form, as well as the silaneoxiamine (Si-O-N). The hexaphenyldisiloxane crystal belonged to the triclinic crystal system with a space group P[1 with combining macron], a = 8.5829(4) A, b = 9.4856(4) A, c = 10.9694(5) A, [small alpha] = 95.951(4)[degree], [small beta] = 90.059(3)[degree], [gamma] = 113.352(4)[degree], the asymmetric unit comprised of Z = 1. The results showed that the synthetic method to obtain silane ether is simple and can be completed in one step, as well as independently of the type of TEMPO and base used. Also, under the same reactions conditions, we prepared the corres