Events The 25th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

10.3390/ecsoc-25-11778 (registering DOI)

This submission belongs to the session S1. General Organic Synthesis of the event The 25th International Electronic Conference on Synthetic Organic Chemistry

Published date

14 Nov, 2021

Academic Editor

Julio A. Seijas

Citation

Richard T Taylor, Benjamin W Gung, Rebecca G Brunner, Isuru M Jayalath, Kate G. E. Bradford, Isoxazoles via Cycloaddition of Terminal Alkynes and Nitrile Oxides (from Oximes), in Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry, 15 November–30 November 2021, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-25-11778

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Isoxazoles via Cycloaddition of Terminal Alkynes and Nitrile Oxides (from Oximes)

Richard T Taylor ¹

Benjamin W Gung ²

Rebecca G Brunner ²

Isuru M Jayalath ²

Kate G. E. Bradford ²

1. Department of Chemistry and Biochemistry, Miami University, Oxford, OH USA, Tonga

2. Department of Chemistry and Biochemistry, Miami University, Oxford, OH USA

Abstract

Conditions for the production of isoxazoles in a one-pot process are presented. Nitrile N-oxides are generated by the oxidation (using hypervalent iodine reagents) of oximes that subsequently undergo 1,3-dipolar cycloaddition with terminal alkynes affording the isoxazoles. From a collection of three terminal alkynes and four aldehydic oximes, 11 distinct isoxazoles were prepared. The effectiveness of various oxidants and solvent systems is discussed, as are side reactions.

Keywords

1,3-dipolar cycloaddition

isoxazoles

hypervalent iodine

Manuscript

Isoxazoles via Cycloaddition of Terminal Alkynes and Nitrile Oxides (from Oximes).pdf

Poster

presentation Isoxazoles via Cycloaddition of Terminal Alkynes and Nitrile Oxides (from Oximes).pdf

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