Synthesis of 4‑Fluoromethylsydnones and their Participation in Alkyne Cycloaddition Reactions

We report the synthesis and some structural studies of 4-trifluoromethyl, 4-difluoromethyl-, and 4-monofluoromethylsydnones. All but the latter compounds are stable and represent effective precursors to a range of pyrazoles after cycloaddition reactions with alkynes. The cycloadditions are generally...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-04, Vol.78 (8), p.4049-4064
Main Authors: Foster, Robert S, Adams, Harry, Jakobi, Harald, Harrity, Joseph P. A
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Catalysis
Cycloaddition Reaction
Molecular Structure
Sydnones - chemical synthesis
Sydnones - chemistry
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Summary:We report the synthesis and some structural studies of 4-trifluoromethyl, 4-difluoromethyl-, and 4-monofluoromethylsydnones. All but the latter compounds are stable and represent effective precursors to a range of pyrazoles after cycloaddition reactions with alkynes. The cycloadditions are generally highly regioselective and provide 5-fluoromethylpyrazole products, although we have observed that Bn-substituted sydnones can provide an unexpected alkyne insertion mode that generates the 3-fluoromethyl isomer.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo400381a