PRODUCTION OF POLYMERS BY AROMATIC DESILYLATION.
Final technical rept. Mar 67-Feb 68,
SUSSEX UNIV BRIGHTON (ENGLAND)
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Aromatic desilylation has been shown to produce polymeric material but yields are low and the polymers intractable, and it must be concluded that the method does not offer a practicable route to useful polymers at present. Two very useful applications of desilylation to the synthesis of important organic intermediates were developed. These are as follows 1 Preparation of unsymmetrical diaryl and aryl alkyl ketones and 2 Preparation of unsymmetrical diaryl sulphones. The latter reaction gives markedly better yields when conducted in dichloromethane or 1,2-dichloroethane rather than carbon disulphide. Destannylation was found to provide an even better route to the unsymmetrical ketones and sulphones, since reaction occurs under milder conditions. For example, benzenesulphonyl chloride and phenyltrimethylstannane react in presence of aluminium chloride in disulphide at -25C to give phenyl p-tolyl sulphone in 55 yield. Nitrodestannylation by copper nitrate in acetic anhydride, was found to provide a means of introducing nitro groups into specific positions in aromatic rings under mild conditions, and this was used in the preparation of the first nitroaryl-tin compound. Author
- Polymer Chemistry