Publication: "Three-Component reaction" with aromatic thioketones, phenyl azide, and dimethyl fumarate
"Three-Component reaction" with aromatic thioketones, phenyl azide, and dimethyl fumarate
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Mlostoń, G., Romański, J., Linden, A., & Heimgartner, H. (1997). “Three-Component reaction” with aromatic thioketones, phenyl azide, and dimethyl fumarate. Helvetica Chimica Acta, 80, 1992–2001. https://doi.org/10.1002/hlca.19970800617
Abstract
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Abstract
The reaction of thiobenzophenone ( = diphenylmethanethione; 8a) or 9H-fluorene-9-thione (8b) and methyl fumarate (9) in excess PhN3 at 80" yields a mixture of diastereoisomeric thiiranes 10 and 11 (Scheme 1). A mechanism involving the initial formation of 1-phenyl-4,5-dihydro-1H-1,2,3-triazole-4,5-dicarboxylate 12 by 1,3-dipolar cycloaddition of PhN3 and 9 is proposed in Scheme 2.The diazo compound13, which is in equilibrium with 12, undergoes a further 1,3-dipolar cycloaddition with thioketones 8 to give 2,5-dihydro-1,3,4-thiadiazole
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- Mlostoń, Grzegorz
- Romański, Jaroslaw
- Heimgartner, Heinz
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Swiss National Science Foundation
F. Hoffmann-La Roche AG, Basel
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Mlostoń, G., Romański, J., Linden, A., & Heimgartner, H. (1997). “Three-Component reaction” with aromatic thioketones, phenyl azide, and dimethyl fumarate. Helvetica Chimica Acta, 80, 1992–2001. https://doi.org/10.1002/hlca.19970800617
