Synthesis and spectroscopic differentiation of 2- and 4-alkoxythiotetronic acids

Gautham Shenoy, Pilho Kim, Michael Goodwin, Quynh Anh Nguyen, Clifton E. Barry, Cynthia S. Dowd

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Abstract

O-Alkylation of thiotetronic acids gives a mixture of 2- and 4-position enol ether products. Comparison of the physical data revealed that UV spectroscopy was the most reliable method of distinguishing between these related ethers. We have determined that 4-position ethers have a distinct absorption between 235-240 nm, while 2-position ethers have two absorbance peaks, one between 205-220 nm and the other between 305-310 nm. This report describes the synthesis and unambiguous characterization of 2- and 4-methoxy-3,5-dimethylthiotetronic acids. The UV absorption properties of several other pairs of thiotetronic acid ethers confirm that these differences are general features that provide a simple method for distinguishing between 2- and 4-substituted isomers.

Original languageEnglish
Pages (from-to)519-527
Number of pages9
JournalHeterocycles
Volume63
Issue number3
Publication statusPublished - 01-03-2004

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this

Shenoy, G., Kim, P., Goodwin, M., Nguyen, Q. A., Barry, C. E., & Dowd, C. S. (2004). Synthesis and spectroscopic differentiation of 2- and 4-alkoxythiotetronic acids. Heterocycles, 63(3), 519-527.