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Polymer-Mediated Pinacol Rearrangements

Christopher Pavlik, Martha D. Morton, Michael B. Smith*

*Department of Chemistry, University of Connecticut, 55 N. Eagleville Rd., Storrs, CT 06269-3060, USA, Email: michael.smithuconn.edu

C. Pavlik, M. D. Morton, M. B. Smith, Synlett, 2011, 2191-2194.

DOI: 10.1055/s-0030-1261148 (free Supporting Information)


Abstract

Both poly(3,4-ethylenedioxythiophene) and poly(pyrrole) mediate a pinacol rearrangement of 1,2-diols to give ketones or aldehydes in comparable yields to those observed for treatment with mineral or Lewis acids. The two-phase reaction medium in hydrocarbon solvents allows facile recovery of the products. Both the polymer and the hydrocarbon solvent may be reused.

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Key Words

pinacol, diol, PEDOT, poly(pyrrole), pinacol rearrangement, green chemistry


ID: J60-Y2011-2660