Étude de la coupure des liaisons o‐si d'éthers siliciés du type en présence d'agent nucléophile et/ou d'acide

Abstract

We report a study on the hydrolytic instability of the oxygen‐silicon bond of the following compounds: p‐tert‐butyldimethylsilyloxytoluène, p‐triméthylsilyloxytoluène and poly(p‐triméthylsilyloxystyrène). The instability occurs in an acidic media: HCl, H−2SO4, CF3CO0H, BF3 or in presence of a salt: KPF6, KAsF6, KSbF6, NaBF4, [CH3(CH2)3]4NF, [CH3(CH2)3]4NBF4, [CH3(CH2)3]4NPF6, [CH3(CH2)3]4N AsF6, [CH3(CH2)3]4NSbF6. A mixture containing both an acid and a salt from those previously discussed can also be used. A number of representative examples is presented. The tert‐butyldimethylsilylether derivatives are much more stable than the trimethylsilylethers. It is shown that the rate of reaction is dependent on the nucleophilicity of anion used in these salts. This simple procedure undoubtedly extends the scope for a preparation of organosilicon resists.