Publication: Unexpected Formation of Dimethylthioketene Cycloadducts in the Reaction of 1,3-Diphenylaziridine-2,2-dicarboxylate with Cyclobutanethione Derivatives
Unexpected Formation of Dimethylthioketene Cycloadducts in the Reaction of 1,3-Diphenylaziridine-2,2-dicarboxylate with Cyclobutanethione Derivatives
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Mlostoń, G., Urbaniak, K., Linden, A., & Heimgartner, H. (2002). Unexpected Formation of Dimethylthioketene Cycloadducts in the Reaction of 1,3-Diphenylaziridine-2,2-dicarboxylate with Cyclobutanethione Derivatives. Helvetica Chimica Acta, 85, 2644–2656. https://doi.org/10.1002/1522-2675(200209)85:9<2644::AID-HLCA2644>3.0.CO;2-V
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Abstract
The reaction of 2,2,4,4-tetramethyl-3-thioxocyclobutanone (1) with cis-1-alkyl-2,3-diphenylaziridines 5 in boiling toluene yielded the expected trans-configured spirocyclic 1,3-thiazolidines 6 (Scheme 1). Analogously, dimethyl trans-1-(4-methoxyphenyl)aziridine-2,3-dicarboxylate (trans-7) reacted with 1 and the corresponding dithione 2, respectively, to give spirocyclic 1,3-thiazolidine-2,4-dicarboxylates 8 (Scheme 2). However, mixtures of cis- and trans-derivatives were obtained in these cases. Unexpectedly, the reaction of 1 with di
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- Mlostoń, Grzegorz
- Urbaniak, Katarzyna
- Heimgartner, Heinz
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Mlostoń, G., Urbaniak, K., Linden, A., & Heimgartner, H. (2002). Unexpected Formation of Dimethylthioketene Cycloadducts in the Reaction of 1,3-Diphenylaziridine-2,2-dicarboxylate with Cyclobutanethione Derivatives. Helvetica Chimica Acta, 85, 2644–2656. https://doi.org/10.1002/1522-2675(200209)85:9<2644::AID-HLCA2644>3.0.CO;2-V
