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Ceric ammonium nitrate
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===As a deprotection reagent=== CAN is traditionally used to release organic ligands from [[metal carbonyl]]s. In the process, the metal is oxidised, CO is evolved, and the organic ligand is released for further manipulation.<ref>L. Brener, J. S. McKennis, and R. Pettit "Cyclobutadiene in Synthesis: ''endo''-Tricyclo[4.4.0.0<sup>2,5</sup>]deca-3,8-diene-7,10-dione" Org. Synth. 1976, 55, 43.{{doi|10.15227/orgsyn.055.0043}}</ref> For example, with the [[Wulff–Dötz reaction]] an alkyne, carbon monoxide, and a chromium [[carbene]] are combined to form a chromium [[half-sandwich complex]]<ref>{{cite journal|last1 = Waters|first1 = M.|first2 = W. D.|last2 = Wulff|title = The Synthesis of Phenols and Quinones via Fischer Carbene Complexes|journal = [[Organic Reactions]]|date = 2008|volume = 70|issue = 2|pages = 121–623|doi = 10.1002/0471264180.or070.02}}</ref><ref>{{cite journal|last1 = Dötz|first1 = K. H.|title = Carbon–Carbon Bond Formation via Carbonyl-Carbene Complexes|journal = [[Pure and Applied Chemistry]]|date = 1983|volume = 55|issue = 11| pages=1689–1706 |doi=10.1351/pac198355111689| s2cid=95165461 |doi-access = free}}</ref> and the phenol ligand can be isolated by mild CAN oxidation. :[[Image:Wulff–Dötz reaction to a chromium half-sandwich complex.png|700px]] CAN is used to cleave ''para''-methoxybenzyl and 3,4-dimethoxybenzyl ethers, which are [[protecting group]]s for alcohols.<ref name="boons">Boons, Geert-Jan.; Hale, Karl J. (2000). ''Organic Synthesis with Carbohydrates'' (1st ed.) Sheffield, England: Sheffield Academic Press. pp.33</ref><ref name="kocienski">Kocienski, Phillip J. (1994). ''Protecting Groups'' Stuttgart, New York Georg Thieme Verlag. pp 8–9, 52–54</ref> Two equivalents of CAN are required for each equivalent of ''para''-methoxybenzyl ether. The alcohol is released, and the ''para''-methoxybenzyl ether converts to ''para''-methoxybenzaldehyde. The balanced equation is as follows: :{{chem2|2 [NH4]2[Ce(NO3)6] + H3COC6H4CH2OR + H2O → 4 NH4+ + 2 Ce(3+) + 12 NO3− + 2 H+ + H3COC6H4CHO + HOR}}
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