Unexpected Surprise in the Reactions of Acetals and Trialkylsilyl Chloride (R₃SiCl): Efficient Deprotection of Aromatic Acyclic Acetals

Abstract

The reaction of acetals with trialkylsilyl chloride (R₃SiCl) leads to the deprotection of the acetal group, resulting in the corresponding carbonyl compounds. Notably, aromatic dialkyl acetals yield the corresponding parent aromatic aldehydes and ketones in good yields. The reaction conditions are very mild, allowing many acid-labile functional groups to survive without any problems. Additionally, we clarified the reaction mechanism through an NMR study.