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 language | English |
|---|---|
| Pages (from-to) | 519-527 |
| Number of pages | 9 |
| Journal | Heterocycles |
| Volume | 63 |
| Issue number | 3 |
| Publication status | Published - 01-03-2004 |
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All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Pharmacology
- Organic Chemistry
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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 journal › Article
TY - JOUR
T1 - Synthesis and spectroscopic differentiation of 2- and 4-alkoxythiotetronic acids
AU - Shenoy, Gautham
AU - Kim, Pilho
AU - Goodwin, Michael
AU - Nguyen, Quynh Anh
AU - Barry, Clifton E.
AU - Dowd, Cynthia S.
PY - 2004/3/1
Y1 - 2004/3/1
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=1342310666&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=1342310666&partnerID=8YFLogxK
M3 - Article
AN - SCOPUS:1342310666
VL - 63
SP - 519
EP - 527
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 3
ER -