SYNTHESIS AND SPECTROSCOPIC DIFFERENTIATION OF 2- AND 4-ALKOXYTHIOTETRONIC ACIDS |
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Authors: | Shenoy Gautham Kim Pilho Goodwin Michael Nguyen Quynh-Anh Barry Clifton E Dowd Cynthia S |
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Institution: | Tuberculosis Research Section, National Institute of Allergy and Infectious Diseases, Rockville, MD 20852 USA; Email: cdowd@niaid.nih.gov. |
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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. |
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