A Click Chemistry Approach to 5,5′-Disubstituted-3,3′-Bisisoxazoles from Dichloroglyoxime and Alkynes: Luminescent Organometallic Iridium and Rhenium Bisisoxazole Complexes

5,5′-Disubstituted-3,3′-bisisoxazoles are prepared in one step by the dropwise addition of aqueous potassium hydrogen carbonate to a mixture of dichloroglyoxime and terminal alkynes. The reaction exhibits a striking preference for the 5,5′-disubstituted 3,3′-bisisoxazole over the 4,5′-regioisomer. O...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-07, Vol.78 (14), p.7298-7304
Main Authors: van der Peet, Phillip L, Connell, Timothy U, Gunawan, Christian, White, Jonathan M, Donnelly, Paul S, Williams, Spencer J
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Click Chemistry
Crystallography, X-Ray
Iridium - chemistry
Isoxazoles - chemical synthesis
Isoxazoles - chemistry
Luminescence
Models, Molecular
Molecular Structure
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Oximes - chemistry
Rhenium - chemistry
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Summary:5,5′-Disubstituted-3,3′-bisisoxazoles are prepared in one step by the dropwise addition of aqueous potassium hydrogen carbonate to a mixture of dichloroglyoxime and terminal alkynes. The reaction exhibits a striking preference for the 5,5′-disubstituted 3,3′-bisisoxazole over the 4,5′-regioisomer. Organometallic iridium and rhenium bisisoxazole complexes are luminescent with emission wavelengths varying depending upon the identity of the 5,5′-substituent (phenyl, butyl).
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4008755