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editLead
editSilyl groups improve thermal stability of molecules. This involves the ability to resist changes to chemical and physical properties at increased temperatures.[1] Silyl groups also improve volatility and decrease polarity of the derivatives.[2]
Protection Chemistry
editAlkyl silyl groups are frequently used as alcohol protecting groups.
Due to the strength of the Si-F bond, fluorides are commonly used to deprotect silyl groups via an SN2 mechanism.[3] The primary deprotecting agent is tetrabutylammonium fluoride (TBAF), as its aliphatic chains in help incorporate F- into organic solvent.[4]
Modifying Reactivity
editAlkyl substituents with higher steric bulk tend decrease the reactivity of the silyl group. Consequently, bulky substituents increase the silyl group's protective abilities. Since more strenuous conditions are required for protection, groups such as TBDMS and TIPS can be used to selectively protect primary alcohols over secondary alcohols.[3]
[Image: Common silyl groups, increasing left to right in steric bulk]
Enolate Trapping
editSilylation can also be used to trap reactive compounds for isolation and identification uses.[3] A common example of this is reacting a silyl chloride to trap enolates. Since enolate-forming reactions can generate unwanted organic or salt byproducts, silylation is a way to isolate reactive enolates.
Silylation affords an enol silyl ether which can be characterized or stored. The original enolate can be reformed upon reaction with an organolithium, or other strong base.
References
edit- ^ "Thermal Stability Science Behind Heat Resistance - Bannari Amman Institute of Technology". 2023-10-09. Retrieved 2024-11-04.
- ^ Pagliano, Enea; Campanella, Beatrice; D'Ulivo, Alessandro; Mester, Zoltán (2018-09-26). "Derivatization chemistries for the determination of inorganic anions and structurally related compounds by gas chromatography - A review". Analytica Chimica Acta. 1025: 12–40. doi:10.1016/j.aca.2018.03.043. ISSN 0003-2670.
- ^ a b c Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012). Organic chemistry (2nd ed.). Oxford: Oxford university press. ISBN 978-0-19-927029-3.
- ^ Paquette, Leo A., ed. (1995). Encyclopedia of reagents for organic synthesis. Chichester ; New York: Wiley. ISBN 978-0-471-93623-7.