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Synlett 2013; 24(12): 1493-1496
DOI: 10.1055/s-0033-1339200
letter
© Georg Thieme Verlag Stuttgart · New York

Horner–Wadsworth–Emmons Reactions in THF: Effect of Hydroperoxide Species

Amanda G. Jarvis
Department of Chemistry, University of York, York YO10 5DD, UK   Fax: +44(1904)322516   Email: ian.fairlamb@york.ac.uk
,
Elizabeth R. Wells
Department of Chemistry, University of York, York YO10 5DD, UK   Fax: +44(1904)322516   Email: ian.fairlamb@york.ac.uk
,
Ian J. S. Fairlamb*
Department of Chemistry, University of York, York YO10 5DD, UK   Fax: +44(1904)322516   Email: ian.fairlamb@york.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 16 April 2013

Accepted after revision: 20 May 2013

Publication Date:
26 June 2013 (online)

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Abstract

Horner–Wadsworth–Emmons (HWE) reactions routinely employ tetrahydrofuran (THF) as the reaction solvent. In this paper we show that THF adducts (derived from THF–hydroperoxide species) of HWE phosphonate ester compounds are formed under microwave irradiation (i.e., under pressure), or in the presence of a reductant [e.g., P(OEt)3] in a conventionally heated reaction.

Key words

alkenes - phosphorus - peroxides - furan - reduction

Supporting Information

    for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
  • Supporting Information
 

  • References and Notes

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      • Due to health and safety restrictions we have been unable to run direct control reactions with THF-OOH. The isolation and purification of THF-OOH has been previously attempted, see:
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    • 18b We do not recommend purification of THF-OOH by distillation – this could be extremely hazardous and dangerous!