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Synlett 1996; 1996(7): 661-662
DOI: 10.1055/s-1996-5564
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Direct Elimination of Epoxides to Dienes with Phosphonium Anhydrides

James B. Hendrickson* , Martin A. Walker, Alexander Varvak, Md. Sajjat Hussoin
  • *Department of Chemistry, Brandeis University, Waltham, Massachusetts 02254-9110, USA
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Publication Date:
31 December 2000 (online)

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Epoxides have been shown to react with triphenylphosphonium anhydride (POP) and triethylamine, undergoing double elimination to form the corresponding dienes. Phosphorus NMR studies suggest a mechanism involving a rapidly equilibrating initial complex which can form a diol bis-phosphonium ether prior to elimination. Simple eliminations of alcohols with this reagent are summarized for comparison.

Epoxides - Elimination - Phosphine oxides - Triflic anhydride - Phosphonium anhydrides