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

Research output: Contribution to journalArticle

13 Citations (Scopus)

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

Fingerprint

Ethers
Acids
Alkylation
Ultraviolet spectroscopy
Isomers
Ether
Spectrum Analysis
thiotetronic acid

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.
Shenoy, Gautham ; Kim, Pilho ; Goodwin, Michael ; Nguyen, Quynh Anh ; Barry, Clifton E. ; Dowd, Cynthia S. / Synthesis and spectroscopic differentiation of 2- and 4-alkoxythiotetronic acids. In: Heterocycles. 2004 ; Vol. 63, No. 3. pp. 519-527.
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Shenoy, G, Kim, P, Goodwin, M, Nguyen, QA, Barry, CE & Dowd, CS 2004, 'Synthesis and spectroscopic differentiation of 2- and 4-alkoxythiotetronic acids', Heterocycles, vol. 63, no. 3, pp. 519-527.

Synthesis and spectroscopic differentiation of 2- and 4-alkoxythiotetronic acids. / Shenoy, Gautham; Kim, Pilho; Goodwin, Michael; Nguyen, Quynh Anh; Barry, Clifton E.; Dowd, Cynthia S.

In: Heterocycles, Vol. 63, No. 3, 01.03.2004, p. 519-527.

Research output: Contribution to journalArticle

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AU - Dowd, Cynthia S.

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AB - 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.

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Shenoy G, Kim P, Goodwin M, Nguyen QA, Barry CE, Dowd CS. Synthesis and spectroscopic differentiation of 2- and 4-alkoxythiotetronic acids. Heterocycles. 2004 Mar 1;63(3):519-527.