Gold-Catalyzed Oxime-Oxime Rearrangement

Date

2015-06-05

Author

Guven, Sinem
Ozer, Merve Sinem
Kaya, Serap
Menges, Nurettin
BALCI, METİN

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The gold-catalyzed reaction of pyrrole and indole oximes having a propargyl group attached to the nitrogen atom was studied. The selective 6-endo-dig mode of cyclization was observed for the terminal alkynes giving rise to the formation of pyrazine N-oxides in the presence of a gold catalyst. However, the reaction with substituted alkyne transferred the oxime functionality intramolecularly from one carbon atom to another via the 7-endo-dig cyclization process. This transformation is unprecedented in the literature and is named an oximeoxime rearrangement.

Subject Keywords

Meyer-Schuster rearrangement, H bond functionalization, One-pot conversion, C triple bonds, Highly efficient, Atom economy, Skeletal rearrangement, Organic-synthesis, Mild conditions, Aldoximes

URI

https://hdl.handle.net/11511/47614

Journal

ORGANIC LETTERS

DOI

https://doi.org/10.1021/acs.orglett.5b01041

Collections

Test and Measurement Center In advanced Technologies (MERKEZ LABORATUVARI), Article

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Citation Formats

S. Guven, M. S. Ozer, S. Kaya, N. Menges, and M. BALCI, “Gold-Catalyzed Oxime-Oxime Rearrangement,” ORGANIC LETTERS, pp. 2660–2663, 2015, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/47614.