Publication: Chemoselectivity of the Reactions of Diazomethanes with 5-Benzylidene-3-phenylrhodanine
Chemoselectivity of the Reactions of Diazomethanes with 5-Benzylidene-3-phenylrhodanine
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Seyfried, M. S., Linden, A., Mlostoń, G., & Heimgartner, H. (2009). Chemoselectivity of the Reactions of Diazomethanes with 5-Benzylidene-3-phenylrhodanine. Helvetica Chimica Acta, 92(9), 1800–1816. https://doi.org/10.1002/hlca.200900149
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The reactions of 5-benzylidene-3-phenylrhodanine (2; rhodanine = 2-thioxo-1,3-thiazolidin-4-one) with diazomethane (7a) and phenyldiazomethane (7b) occurred chemoselectively at the exocyclic C=C bond to give the spirocyclopropane derivatives 9 and, in the case of 7a, also the C-methylated products 8 (Scheme 1). In contrast, diphenyldiazomethane (7c) reacted exclusively with the C=S group leading to the 2-(diphenylmethylidene)-1,3-thiazolidine 11 via [2+3] cycloaddition and a two-fold extrusion reaction. Treatment of 8 or 9b with an e
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- Seyfried, M S
- Heimgartner, H
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Citations
Seyfried, M. S., Linden, A., Mlostoń, G., & Heimgartner, H. (2009). Chemoselectivity of the Reactions of Diazomethanes with 5-Benzylidene-3-phenylrhodanine. Helvetica Chimica Acta, 92(9), 1800–1816. https://doi.org/10.1002/hlca.200900149
