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Synfacts 2006(10): 1009-1009  
DOI: 10.1055/s-2006-949358
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Polymerization of Diazo Esters

Contributor(s): Timothy M. Swager, Mark S. Taylor
D. G. H. Hetterscheid, C. Hendriksen, W. I. Dzik, J. M. M. Smits, E. R. H. van Eck, A. E. Rowan, V. Busico, M. Vacatello, V. V. A. Castelli, A. Segre, E. Jellema, T. G. Bloemberg, B. de Bruin*
Radboud University, Nijmegen and University of Amsterdam, The Netherlands; Università di Napoli and Istituto di Metodologie Chimiche, Montelibretti, Italy
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

During their investigations of the reactivity of diazo compounds catalyzed by rhodium(I) complexes, the authors observed the formation of high-molecular-weight (up to 190 kDa), stereoregular poly(ethyl 2-ylidene-acetate) from ethyl diazoacetate. Several rhodium- and iridium-based catalysts 1-4 mediate this polymerization in moderate yield (10-50%), with polydispersity values between 2 and 3. Variation of the structure of the diazo ester is tolerated, albeit at the expense of polymer yield. The authors suggest a syndiotactic architecture for this new material, although more data are needed for definitive stereochemical assignment.