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Grubbs' Catalyst in Paraffin: An Air-Stable Preparation for Alkene Metathesis

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Douglass F. Taber* and Kevin J. Frankowski

Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716 taberdf@udel.edu

J. Org. Chem., 2003, 68 (15), pp 6047–6048

DOI: 10.1021/jo030005p

Publication Date (Web): June 28, 2003

Section:

Aliphatic Compounds

Abstract

A homogeneous mixture of Grubbs' catalyst in paraffin wax was shown to catalyze three important types of metathesis reactions: ring-closing metathesis, alkene dimerization, and alkene cross-metathesis (e.g., 11 → 13). This catalyst preparation demonstrated no loss in catalytic activity after 22 months of storage open to the air.

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Citing Articles

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

Synthesis and RCM Reactions Using a Recyclable Grubbs−Hoveyda Metathesis Catalyst Activated by a Light Fluorous Tag
Masato Matsugi, Yuki Kobayashi, Naoki Suzumura, Yuki Tsuchiya, and Takayuki Shioiri
The Journal of Organic Chemistry2010 75 (22), 7905-7908
- Synthesis and RCM Reactions Using a Recyclable Grubbs−Hoveyda Metathesis Catalyst Activated by a Light Fluorous Tag
  Masato Matsugi, Yuki Kobayashi, Naoki Suzumura, Yuki Tsuchiya, and Takayuki Shioiri
  The Journal of Organic Chemistry2010 75 (22), 7905-7908
  A recyclable Grubbs−Hoveyda second-generation catalyst activated by a light fluorous tag was prepared. The modified light fluorous catalyst exhibited higher catalytic activity than the parent or the previously reported light fluorous variant for RCM ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Polymer-Supported Well-Defined Metathesis Catalysts
Michael R. Buchmeiser
Chemical Reviews2009 109 (2), 303-321
- Polymer-Supported Well-Defined Metathesis Catalysts
  Michael R. Buchmeiser
  Chemical Reviews2009 109 (2), 303-321
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Potassium Hydride in Paraffin: A Useful Base for Organic Synthesis
Douglass F. Taber and Christopher G. Nelson
The Journal of Organic Chemistry2006 71 (23), 8973-8974
- Potassium Hydride in Paraffin: A Useful Base for Organic Synthesis
  Douglass F. Taber and Christopher G. Nelson
  The Journal of Organic Chemistry2006 71 (23), 8973-8974
  The preparation of potassium hydride as a 1:1 homogenate with paraffin, termed KH(P), is reported. KH(P), a solid at room temperature, is stable without special handling. On suspension in THF with a phosphonium salt, KH(P) rapidly generates the ylide. ...
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Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab
Douglass F. Taber and Kevin J. Frankowski
Journal of Chemical Education2006 83 (2), 283
- Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab
  Douglass F. Taber and Kevin J. Frankowski
  Journal of Chemical Education2006 83 (2), 283
  An experiment for the undergraduate organic laboratory course, the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol, is described in detail. The Grubbs' catalyst is dispersed in paraffin wax to eliminate the need for inert ...
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