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Self-Terminating, Oxidative Radical Cyclizations: A Novel Reaction of Acyloxyl Radicals
Abstract
Acyloxyl radicals RC(O)O* (with R = alkyl, aryl) could be trapped through addition to cyclic and open-chain alkynes, where they were found to act as a donor of oxygen atoms. Mechanistically, this radical oxygenation proceeded through a transannular or intramolecular, respectively, radical cyclization cascade, which was finally terminated by release of an acyl radical RC*(O). The reaction led to stereoselective formation of cyclized products, which contained a carbonyl group at the former site of the alkyne triple bond.
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Citations
Cited by
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Shape Control of Colloidal Metal Nanocrystals
Tao, A. R., Habas, S., & Yang, P. (2008) · Small · doi:10.1002/smll.200701295 · Cited by 2,408
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Balasubramanian, K., & Burghard, M. (2005) · Small · doi:10.1002/smll.200400118 · Cited by 1,769
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Wiley, B., Sun, Y., Mayers, B., & Xia, Y. (2005) · Chemistry – A European Journal · doi:10.1002/chem.200400927 · Cited by 1,643
Coates, G. W., & Moore, D. R. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200460442 · Cited by 1,154
Metadata
- Authors
- Wille, U.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2001-12-08
- Volume
- 124
- Issue
- 1
- Pages
- 14-15
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1969449710
- Cited by
- 183
- References
- 0
- FWCI
- 15.51
- Type
- journal article
- Language
- en
- Open access
- closed
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