Synthesis and polymerization of 5‐(N,N‐dimethylamino)naphthylacetylene with homogeneous rhodium and palladium complexes |
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Authors: | J Gonzalo Rodríguez Jose Luis Tejedor |
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Institution: | Departamento de Química Orgánica, Universidad Autónoma, Cantoblanco 28049 Madrid, Spain |
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Abstract: | The monomer 5‐ethynyl‐N,N‐dimethylnaphthalen‐1‐amine ( 2 ) was satisfactorily obtained by a heterocoupling reaction between 5‐iodo‐(N,N‐dimethyl)naphthalen‐1‐amine and 2‐methyl‐3‐butyn‐2‐ol catalyzed by a palladium–copper system and followed by acetone elimination. Poly(5‐ethynyl‐N,N‐dimethylnaphthalen‐1‐amine) was isolated by the reaction of 2 in the presence of homogeneous rhodium and palladium complexes. On the basis of the spectroscopic data, the polymer always showed a cis–transoidal, stereoregular structure. Moreover, only with the rhodium catalyst in methanol was a dimeric product isolated in a very low yield, having a conjugated terminal ene–yne structure, which permitted the consideration of a metallated chain‐transfer intermediate in the polymer propagation. The kinetics of the catalyzed reaction were analyzed. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 45: 437–446, 2007 |
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Keywords: | bis(rhodium chloride cycloocta‐1 5‐diene) catalyst 5‐ethynyl‐N N‐dimethylnaphthalen‐1‐amine fluorescence organometallic catalyst palladium– chlorotrimethylsilane polyacetylenes structure of the polymers |
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