r37980778c78--ac2548392b4ad4d785bc599015d0208f

3-Aryl-3-hydroxy-1-methylazetidine-2-thiones react with HCl in DMSO to give 3-methyl-5-aryloxazole-2-thiones. Substituent effects correlate with rate effects on hydrolyses of acetals of benzaldehyde. An 17O labeling experiment indicates that the oxygen atom of the product is derived from the hydroxyl group. Trifluoroacetic anhydride/DMSO in CH2Cl2 can also promote the reaction. Mechanisms involving a Grob-type fragmentation of an activated substrate, followed by recyclization, or a cyclopropylcarbinyl type of rearrangement can account for this oxidative rearrangement.

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PID https://www.doi.org/10.1021/ol802050a.s001
URL https://figshare.com/articles/journal_contribution/Hydroxy_Thiolactams_to_Oxazole_2_thiones_A_Novel_DMSO_Promoted_Oxidation/2902693
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Collected From figshare
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Publication Date 2016-02-27
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Source https://science-innovation-policy.openaire.eu/search/publication?articleId=r37980778c78::ac2548392b4ad4d785bc599015d0208f
Author jsonws_user
Last Updated 21 December 2020, 20:02 (CET)
Created 21 December 2020, 20:02 (CET)