Heterocycles 2014-08-15

SYNTHESIS AND SPECTROSCOPIC DIFFERENTIATION OF 2- AND 4-ALKOXYTHIOTETRONIC ACIDS.

Abhijit A Patil, Parag Sayal, Marie-Lise Depondt, Ryan D Beveridge, Anthony Roylance, Deepti H Kriplani, Katie N Myers, Angela Cox, David Jellinek, Malee Fernando, Thomas A Carroll, Spencer J Collis

Index: Heterocycles 63 , 5-8, (2004)

Full Text: HTML

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.

Related Compounds

  • DICHLORO(O-IS...

Related Articles:

Ruthenium-based heterocyclic carbene-coordinated olefin metathesis catalysts.

2010-03-10

[Chem. Rev. 110 , 1746, (2010)]

Olefin Metathesis and Beyond A list of abbreviations can be found at the end of this article.

2000-10-01

[Angew. Chem. Int. Ed. Engl. 39 , 3012, (2000)]

The development of L2X2Ru=CHR olefin metathesis catalysts: an organometallic success story.

2001-01-01

[Acc. Chem. Res. 34 , 18, (2001)]

Sequential catalysis: a metathesis/dihydroxylation sequence.

2006-03-13

[Angew. Chem. Int. Ed. Engl. 45 , 1900, (2006)]

Efficient large-scale synthesis of BILN 2061, a potent HCV protease inhibitor, by a convergent approach based on ring-closing metathesis.

2006-09-15

[J. Org. Chem. 71 , 7133, (2006)]

More Articles...