Syntheses and reactions of (trimethylsiloxy)benzoyl chlorides

Abstract

Abstract The (trimethylsiloxy)benzoyl chlorides 1–7 are easily to obtain under mild conditions from silylated hydroxybenzoic acids by means of thionyl chloride. Whereas these acid chlorides are stable at room temperature, they undergo condensation polymerization at temperatures above 100°C. Reactions with various nucleophils, such as thioalcohols, phenols, amines, N,O ‐bis(silylated) amino acids and N ‐silylated lactams were investigated. With hexamethyldisilazane and thionyl chloride the (trimethylsiloxy)benzonitriles 21, 22 are accessible, and by means of trimethylsilyl azide the (trimethylsiloxy)phenyl isocyanates 23–25 were obtained. Conversion with phenyl carbazate and subsequent silylation lead to the 2‐(trimethylsiloxy)phenyl‐1,3,4‐oxadiazol‐5‐ones 27a‐c .