Abstract
Abstract The ambidentate substrate chloromethyldimethylchlorosilane reacts with carboxylates to form both the mono and bis derivatives C1CH2Si(CH3)2O2CR RCO2CH2Si(CH3)2O2CR depending on the experimental conditions. Reaction in THF at room temperature favors the mono derivative, while reflux in DMF produces the bis derivatives. When the group attached to the carbonyl is large, reaction at room temperature is very slow and in refluxing DMF a mixture of mono and bis derivatives is formed. Transsilylation of trimethylsilylbenzoate with chloromethyldimethylchlorosilane produces the mono derivative. Attempts to make the mono carbon substituted derivative failed. The IR of all derivatives contain normal ester carbonyl stretching vibrations and therefore none have coordination to silicon.
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