Polymer-mediated pinacol rearrangements

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

Research output: Contribution to journalArticle

7 Citations (Scopus)

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.

Original languageEnglish (US)
Article numberS04511ST
Pages (from-to)2191-2194
Number of pages4
JournalSynlett
Issue number15
DOIs
StatePublished - Sep 2 2011

Fingerprint

Polymers
Hydrocarbons
Lewis Acids
Pyrroles
Ketones
Aldehydes
Minerals
Recovery
Acids
poly(3,4-ethylene dioxythiophene)

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Pavlik, C., Morton, M. D., & Smith, M. B. (2011). Polymer-mediated pinacol rearrangements. Synlett, (15), 2191-2194. [S04511ST]. https://doi.org/10.1055/s-0030-1261148

Polymer-mediated pinacol rearrangements. / Pavlik, Christopher; Morton, Martha D.; Smith, Michael B.

In: Synlett, No. 15, S04511ST, 02.09.2011, p. 2191-2194.

Research output: Contribution to journalArticle

Pavlik, C, Morton, MD & Smith, MB 2011, 'Polymer-mediated pinacol rearrangements', Synlett, no. 15, S04511ST, pp. 2191-2194. https://doi.org/10.1055/s-0030-1261148
Pavlik, Christopher ; Morton, Martha D. ; Smith, Michael B. / Polymer-mediated pinacol rearrangements. In: Synlett. 2011 ; No. 15. pp. 2191-2194.
@article{c52a83dfcdeb4b0dbd72f09bd2c9f2a8,
title = "Polymer-mediated pinacol rearrangements",
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.",
keywords = "PEDOT, diol, pinacol, poly(pyrrole), rearrangement",
author = "Christopher Pavlik and Morton, {Martha D.} and Smith, {Michael B.}",
year = "2011",
month = "9",
day = "2",
doi = "10.1055/s-0030-1261148",
language = "English (US)",
pages = "2191--2194",
journal = "Synlett",
issn = "0936-5214",
publisher = "Georg Thieme Verlag",
number = "15",

}

TY - JOUR

T1 - Polymer-mediated pinacol rearrangements

AU - Pavlik, Christopher

AU - Morton, Martha D.

AU - Smith, Michael B.

PY - 2011/9/2

Y1 - 2011/9/2

N2 - 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.

AB - 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.

KW - PEDOT

KW - diol

KW - pinacol

KW - poly(pyrrole)

KW - rearrangement

UR - http://www.scopus.com/inward/record.url?scp=80052670503&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80052670503&partnerID=8YFLogxK

U2 - 10.1055/s-0030-1261148

DO - 10.1055/s-0030-1261148

M3 - Article

AN - SCOPUS:80052670503

SP - 2191

EP - 2194

JO - Synlett

JF - Synlett

SN - 0936-5214

IS - 15

M1 - S04511ST

ER -