ChemInform Abstract: Selectivity of the Si-C Cleavage in Compounds of Type Me3SiCH2-R.
Abstract
The regiochemistry of the electrophilic cleavage of the sp3-Si-Cbond in the Compounds Me3SiCH2-R (R: -Me, -Cl, -Pr, -COOEI) and Me3SiCHCl2 is investigated using ICI, Me3SiOSO2CI and CI-SO3H as electrophiles.
ChemInform Abstract
The regiochemistry of the electrophilic cleavage of the sp3-Si-Cbond in the Compounds Me3SiCH2-R (R: -Me, -Cl, -Pr, -COOEI) and Me3SiCHCl2 is investigated using ICI, Me3SiOSO2CI and CI-SO3H as electrophiles. When the substituent is -Cl or -Pr, a regioselective cleavage of the Si- CH3 bond is observed and silylated chlorosulfonates or sulfates are produced. ln the case of R: -COOEt, a regioselective Splitting of the Si-CH2COOEt bond is observed. The synthetic potential of ethyl trimethylsilylacetate is confirmed by the facile synthesis of ethyl iodoacetate.
