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Keto Furanylidene Building Blocks from Silyl Ethers of Monoalkynylated β- Keto Carbonyls with Iron(III) Chloride Hexahydrate-Iodine
Heterocyclic Communications
  • Brittany Garner, Georgia Southern University
  • Kristina Deveaux, Georgia Southern University
  • Laura Gessner, Georgia Southern University
  • Julia Trossarello, Georgia Southern University
  • Shuting Dai, Georgia Southern University
  • James W. Morgan, Georgia Southern University
  • Karelle Aiken, Georgia Southern University
Document Type
Article
Publication Date
1-1-2012
DOI
10.1515/hc-2012-0069
Disciplines
Abstract

Keto furanylidene building blocks are synthesized from the unique silyl ethers of monoalkynylated β-keto carbonyls. The procedure consists of a desilylation, cyclization, and alkyne hydration facilitated by either a one-pot reaction with iron(III) chloride hexahydrate-iodine or a two-step procedure with tosylic acid and gold(I) chloride. Notably, the hydration of the terminal alkyne with iron(III) chloride hexahydrate-iodine reagent is a safer and new alternative to the use of mercury(II) salts.

Citation Information
Brittany Garner, Kristina Deveaux, Laura Gessner, Julia Trossarello, et al.. "Keto Furanylidene Building Blocks from Silyl Ethers of Monoalkynylated β- Keto Carbonyls with Iron(III) Chloride Hexahydrate-Iodine" Heterocyclic Communications Vol. 18 Iss. 4 (2012) p. 181 - 187 ISSN: 2191-0197
Available at: http://works.bepress.com/karelle_aiken/15/