Reactions of Trimethylsilanol and other Trialkyl-, Alkylaryl-, or Triarylsilanols

Reactions of Trimethylsilanol and other Trialkyl-, Alkylaryl-, or Triarylsilanols 

To mention a few synthetic appHcations of trialkylsilanols, trimethylsilanol 4 adds readily to 2-chloroacrylonitrile in diethyl ether in the presence of triethylamine as triethylammonium trimethylsilanolate followed by ehmination of triethylamine hydrochloride to give 99 [32] (cf. discussion of the strongly nucleophihc properties of ammonium trimethylsilanolate 155 in Section 4.2.1). The stable potassium trimethylsilanolate 97 has also been used for the saponification of esters (Section 4.7). Dimethylphenylsilanol 100 adds readily to a,y9-unsaturated carbonyl compounds such as methyl vinyl ketone 764 in the presence of Pd(OAc)2 in a Heck-Suzuki-type reaction to give the sihcon-free /9-phenylmethylvinylketone 101 [33]. 

Bulkiness HjSiO- H2Si(Me)0- HSi(Me)20- MegSiO- EtgSiO- tert.BuSi(Me)2SiO- tert.BuSiPhgO- i-PrgSiO 

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