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Silyl Groups as Protecting Groups

A widely used method of protecting hydroxyl groups in organic molecules is to turn them into silyl ethers. A protecting group is one which reduces the reactivity of the functional group it protects so that chemistry may be carried out elsewhere on the molecule without fear of interference from the protected group.


Recall from the first page of this chapter that silicon stabilises carbocations β to it and carbanions α to it. Thus vinylsilanes can undergo both electrophilic substitution and nucleophilic addition.

Silyl Enol Ethers

Whereas enols are seen only as a small proportion of the keto-enol tautomerism, silyl enol ethers are stable and very useful sources of regiochemically pure enolate ions.

Introduction to Organosilicon Chemistry

Silicon forms very strong bonds to oxygen and fluorine (particularly to oxygen) - this provides a driving force for much of silicon's chemistry.