Publication: 1,5-Dipolar electrocyclizations in reactions of alpha-Thioxo Ketones and alpha-Thioxo Thioamides with Diazo compounds
1,5-Dipolar electrocyclizations in reactions of alpha-Thioxo Ketones and alpha-Thioxo Thioamides with Diazo compounds
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Egli, D. H., Linden, A., & Heimgartner, H. (2006). 1,5-Dipolar electrocyclizations in reactions of alpha-Thioxo Ketones and alpha-Thioxo Thioamides with Diazo compounds. Helvetica Chimica Acta, 89(9), 1910–1926. https://doi.org/10.1002/hlca.200690182
Abstract
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Abstract
Several reactions of a-thioxo ketones and a-thioxo thioamides with diazo compounds were investigated. Most of them proceeded via a reactive thiocarbonyl ylide, which underwent a [2+3] cycloaddition with the a-thioxo ketone to give the 'Schönberg products' 17–19 or a 1,5-dipolar electrocyclization to give the corresponding five membered 1,3-oxathioles (i.e., 13, 20a, 20b, 21, and 25) and 1,3-dithioles (i.e., 33, 34, and 35), respectively. In the case of thioamide 32, the thiocarbonyl ylides underwent a competitive 1,3-dipolar electrocy
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- Egli, D H
- Heimgartner, H
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Egli, D. H., Linden, A., & Heimgartner, H. (2006). 1,5-Dipolar electrocyclizations in reactions of alpha-Thioxo Ketones and alpha-Thioxo Thioamides with Diazo compounds. Helvetica Chimica Acta, 89(9), 1910–1926. https://doi.org/10.1002/hlca.200690182
