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Bismuth Compounds in Organic Synthesis: Synthesis of Dioxanes, Dioxepines, and Dioxolanes Catalyzed by Bismuth(III) Triflate
Synthesis (2010)
  • Ram S. Mohan, Illinois Wesleyan University
  • Daniel M. Podgorski
  • Scott W. Krabbe
  • Long N. Le
  • Paul R. Sierszulski
Abstract

A simple method for the synthesis of l,3-dioxolanes from carbonyl compounds has been developed using l,2-bis(trimethylsilyloxy) ethane in the presence of bismuth (III) triflate as a catalyst. The bismuth(III) triflate catalyzed synthesis of a range of dioxanes and dioxepines has also been developed. In these latter cases, the carbonyl compound is treated with a diol, and triethyl orthoformate is used as a water scavenger. All these methods avoid the use of a Dean-Stark trap.

Keywords
  • Aldehydes,
  • ketones,
  • protection,
  • cyclic acetals,
  • l,
  • 2-bis(trimethylsilyloxy)ethane.
Disciplines
Publication Date
2010
Citation Information
Ram S. Mohan, Daniel M. Podgorski, Scott W. Krabbe, Long N. Le, et al.. "Bismuth Compounds in Organic Synthesis: Synthesis of Dioxanes, Dioxepines, and Dioxolanes Catalyzed by Bismuth(III) Triflate" Synthesis Iss. 16 (2010)
Available at: http://works.bepress.com/ram_mohan/32/