Published January 28, 2015
| Supplemental Material
Journal Article
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Direct Generation of Oxygen-Stabilized Radicals by H• Transfer from Transition Metal Hydrides
Chicago
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Abstract
Transition-metal hydrides generate α-alkoxy radicals by H• transfer to enol ethers. We have measured the rate constant for transfer from CpCr(CO)_3H to n-butyl vinyl ether and have examined the chemistry of radicals generated by such transfers. Radicals from appropriate substrates undergo 5-exo cyclization, with higher diastereoselectivity than the analogous all-carbon radicals. From such radicals it is straightforward to make substituted tetrahydrofurans.
Additional Information
© 2015 American Chemical Society. Received: November 19, 2014; Published: January 8, 2015. This material is based upon work supported by the National Science Foundation under Grant No. CHE-1401049 (IUPAC Novel Molecular and Supramolecular Theory and Synthesis Approaches for Sustainable Catalysis). J.L.K. acknowledges the National Science Foundation Graduate Research Fellowship Program. The authors are grateful to Scott A. Snyder, Deven P. Estes, and Gang Li for helpful discussions. Kevin D. Vo is acknowledged for the synthesis of starting materials.Attached Files
Supplemental Material - ja511883b_si_001.pdf
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Additional details
- Eprint ID
- 55745
- DOI
- 10.1021/ja511883b
- Resolver ID
- CaltechAUTHORS:20150313-103641415
- NSF
- CHE-1401049
- NSF Graduate Research Fellowship
- Created
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2015-03-13Created from EPrint's datestamp field
- Updated
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2021-11-10Created from EPrint's last_modified field