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Synthesis 1998; 1998(4): 417-422
DOI: 10.1055/s-1998-2053
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Synthesis of 1,3,5-Trioxanes: Catalytic Cyclotrimerization of Aldehydes

Zuolin Zhu* , James H. Espenson
  • *Ames Laboratory and Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA; Fax + 1 (5 15)2 94 52 33; E-mail: espenson@ameslab.gov
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Publication History

Publication Date:
31 December 2000 (online)

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A series of 1,3,5-trioxanes derived from a single aldehyde, or from two aldehydes, were synthesized with methylrhenium trioxide as a catalyst. Cyclotrimerization of the aldehydes gave excellent yields under proper conditions, as did diethyl ketomalonate. A possible intermediate in the case of propionaldehyde was observed using 1H NMR spectroscopy. Water inhibits both forward and reverse reactions.

methylrhenium trioxide (MTO) - 1,3,5-trioxane - catalytic cyclotrimerization