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Syntheses and reactions of (trimethylsiloxy)benzoyl chlorides
Author(s) -
Schwarz Gerd,
Alberts Heinrich,
Kricheldorf Hans R.
Publication year - 1981
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198119810713
Subject(s) - chemistry , thionyl chloride , silylation , benzoyl chloride , trimethylsilyl azide , trimethylsilyl , organic chemistry , chloride , condensation , polymer chemistry , azide , catalysis , physics , thermodynamics
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 .