Journal
ORGANIC LETTERS
Volume 10, Issue 21, Pages 4975-4978Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802050a
Keywords
-
Categories
Funding
- National Science Foundation
Ask authors/readers for more resources
3-Aryl-3-hydroxy-l-methylazetidine-2-thiones react with HCl in DMSO to give 3-methyl-5-aryloxazole-2-thiones. Substituent effects correlatewith rate effects on hydrolyses of acetals of benzaldehyde. An (17)O labeling experiment indicates that the oxygen atom of the product is derived from the hydroxyl group. Trifluoroacetic anhydride/DMSO in CH(2)Cl(2) 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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available