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Synlett 2011(15): 2191-2194  
DOI: 10.1055/s-0030-1261148
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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
Fax: +1(860)4862981; e-Mail: michael.smith@uconn.edu;
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Publikationsverlauf

Received 16 May 2011
Publikationsdatum:
31. August 2011 (online)

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Abstract

Both poly(3,4-ethylenedioxythiophene) and poly(pyrrole) mediate a pinacol rearrangement of 1,2-diols. The yields of ketone or aldehyde products are comparable to those observed for treatment with mineral acids or Lewis acids. The advantage of this protocol is a two-phase reaction medium in hydrocarbon solvents that allows facile recovery of the products by simple filtration of the polymer and removal of solvents. Both the polymer and the hydrocarbon solvent may be recovered and used in subsequent reactions.

Key words

pinacol - diol - PEDOT - poly(pyrrole) - rearrangement

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