The formation of a peracetal and trioxane from an enol ether with Copper(II) triflate and oxygen: unexpected oxygenation of aldol intermediates
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In vitro experiments have shown that 481 can undergo spontaneous conversion to a transient enol as proposed in step ii).
“These in vitro experiments have shown that 481 can indeed undergo sponataneous conversion to a transient enol as proposed in step ii) of Scheme 11 [204,238,243,302,303]”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [302]
Cites
Solvolytic routes via alkylcopper intermediates in the electron-transfer oxidation of alkyl radicals
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Self-citationVonwiller, S. C., Warner, J. A., Mann, S. T., & Haynes, R. K. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00150a009 · Cited by 48 · see citing works
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Haynes, R. K., & Vonwiller, S. C. (1992) · Synlett · doi:10.1055/s-1992-21384 · Cited by 36 · see citing works
Polarographic evidence for the stability of copper(I) ion in some non-complexing nonaqueous solvents
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Synthesis of tricyclic arteannuin-like compounds
Jefford, C. W., Velarde, J., & Bernardinelli, G. H. (1989) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)80724-3 · Cited by 34 · see citing works
Synthesis of 1,2-dioxetanes via electron-transfer oxygenation
Curci, R., Lopez, L., Troisi, L., RASHID, S. M. K., & Schaap, A. P. (1987) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)96719-4 · Cited by 22 · see citing works
A New Reaction of 1,2‐Dioxetanes. Formation of 1,2,4‐Trioxanes from Aldehydes
Jefford, C. W., Boukouvalas, J., & Kohmoto, S. (1983) · Helvetica Chimica Acta · doi:10.1002/hlca.19830660828 · Cited by 22 · see citing works
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The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao)
Brown, G. D. (2010) · Molecules · doi:10.3390/molecules15117603 · Cited by 363 · see citing works
Dussault, P. H., Lee, H., & Liu, X. (2000) · Journal of the Chemical Society Perkin Transactions 1 · doi:10.1039/b001391i · Cited by 41 · see citing works
Korshin, E. E., & Bachi, M. D. (2009) · Patai's chemistry of functional groups · doi:10.1002/9780470682531.pat0351 · Cited by 8 · see citing works
Copper(II) Trifluoromethanesulfonate
Laali, K. K., Sarca, V. D., & Ollevier, T. (2016) · Encyclopedia of Reagents for Organic Synthesis · doi:10.1002/047084289x.rc250.pub3
Copper(II) Trifluoromethanesulfonate
Laali, K. K., Sarca, V. D., & Laali, K. K. (2007) · Encyclopedia of Reagents for Organic Synthesis · doi:10.1002/9780470842898.rc250.pub2
Copper(II) Trifluoromethanesulfonate
Laali, K. K., Sarca, V. D., & Laali, K. K. (2007) · Encyclopedia of Reagents for Organic Synthesis · doi:10.1002/047084289x.rc250.pub2
- Authors
- Vonwiller, S. C., Warner, J. A., Mann, S. T., & Haynes, R. K.
- Affiliations
- The University of Sydney (AU)
- Hong Kong University of Science and Technology (HK)
- ORCID
- Haynes, Richard K.
- Venue
- Tetrahedron Letters
- Publisher
- Elsevier BV
- Published
- 1997-03
- Volume
- 38
- Issue
- 13
- Pages
- 2363-2366
- ISSN
- 0040-4039 (ISSN-L)
- OpenAlex
- W1978577888
- Cited by
- 5
- References
- 16
- Citations by year
- 2016: 1
- FWCI
- 0.30
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Tetrahedron Letters (publishedVersion)
- Rare & Special e-Zone (The Hong Kong University of Science and Technology) (submittedVersion)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Oxidative Organic Chemistry Reactions
- Physical Sciences › Chemistry › Inorganic Chemistry › Metal-Catalyzed Oxygenation Mechanisms
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Keywords
- enol ethers, copper(II) triflate, oxygenation, ketoaldehydes
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Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
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