Citation:
Guowen Xing, Guangjian Liu, Le Chang. Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching[J]. University Chemistry,
;2025, 40(4): 282-290.
doi:
10.12461/PKU.DXHX202407058
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Carbonyl oxonium intermediates are highly reactive and prone to a variety of reactions. This paper outlines five key types of reactions involving carbonyl oxonium intermediates in university-level organic chemistry education: addition, substitution, decomposition, isomerization, and pericyclic reactions. The role of carbonyl oxonium as a crucial intermediate in the mechanisms of complex organic reactions is discussed. It is important to note that the reactivity of carbonyl oxonium is multifaceted and subject to competition and coexistence among these different reaction types. A thorough understanding of these five reactions enhances scientific reasoning and literacy in organic chemistry, aligning with the educational philosophy that “organic chemistry is both a science and an art”.
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Keywords:
- Organic chemistry,
- Carbonyl group,
- Oxonium,
- Reaction mechanism
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[1]
Kwanruthai, T.; Rychnovsky, S. D. Org. Lett. 2008, 10, 4839.
-
[2]
Li, L.; Ni, C.; Wang, F.; Hu, J. Nat. Commun. 2016, 7, 13320.
-
[3]
Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Salisbury, UK, 2012, p. 468.
-
[4]
Camp, J. E. ChemSusChem. 2018, 11, 3048
-
[5]
Li, Z.; Tong, R. J. Org. Chem. 2016, 81, 4847.
-
[6]
Hong, S.; McIntosh, M. C. Org. Lett. 2002, 4, 19.
-
[7]
Ghosh, A. K.; Yadav, M. J. Org. Chem. 2021, 86, 8127.
-
[8]
a) Volkmann, R. A.; Weeks, P. D.; Kuhla, D. E.; Whipple, E. B.; Chmurny, G. N. J. Org. Chem. 1977, 42, 3976. b) Garst, M. E.; McBride, B. J.; Douglass, J. G. Tetrahedron Lett. 1983, 24, 1675.
-
[9]
Baldwin, J. E.; Mayweg, A. V. W.; Neumann, K.; Pritchard, G. J. Org. Lett. 1999, 1, 1933.
-
[10]
Li, G.; Huang, X.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 6944.
-
[11]
Hsu, Y.-C.; Ting, C.-M.; Liu, R.-S. J. Am. Chem. Soc. 2009, 131, 2090.
-
[12]
-
[13]
-
[1]
-
-
-
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