Cyclotene resins

The synthesis of the monomer for Cyclotene resins (Equation 13) is accompanied by the formation of by-products that derive from internal rather than terminal aryl attack on the vinyl group. Further decrease of selectivity is caused by aryl attack on only one of the terminal carbon atoms of the two siloxane vinyl groups and by hydrogenolysis at the C-Si bond carbons, followed by aryl group attack on the terminal or the internal carbon atom of the vinyl group thus formed. 

Some intermediates to fine chemicals are prepared industrially by vinylation of aromatics. We have selected three well-known products as representative cases, namely an intermediate to Naproxen, a non-steroidal antirheumatic drug (Albermarle) (Equation 11) an intermediate to Prosulfuron, a potent herbicide (Ciba Geigy-Novartis) (Equation 12) and a monomer for polymerization to Cyclotene electronic resins (Dow Chemicals) (Equation 13). 

Patrick, D.W. Strand, D.A. Cortes, H.J. Automation and optimization of multidimensional microcolumn size exclusion chromatography-liquid chromatography for the analysis of photocrosslinkers in Cyclotene 400 series advanced electronic resins. J. Sep. Sci. 2002, 25, 519-526. 

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