A novel approach to 1,4-oxathiocines: the thermal rearrangement of thiophenium methylides
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 2,p. 138-140
- https://doi.org/10.1039/c39880000138
Abstract
2,5-Disubstituted thiophenes react at ambient temperature under rhodium acetate catalysis with various diazoketones to give thiophenium methylides which rearrange thermally to give 1,4-oxathiocines, as confirmed by an X-ray crystal structure determination; one of these, 3-ethoxycarbonyl-5,8-dichloro-2-methyl-1,4-oxathiocine, corrects a supposed cyclopropathiophene structure and further rearranges to give ethyl 2,4-dichloro-5-hydroxy-6-methylbenzoate.Keywords
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