Editing Ceric ammonium nitrate (section)

==Applications in organic chemistry==
In organic synthesis, CAN is useful as an oxidant for many functional groups ([[alcohols]], [[phenol]]s, and [[ether]]s) as well as C–H bonds, especially those that are benzylic. [[Alkene]]s undergo dinitroxylation, although the outcome is solvent-dependent. [[Quinone]]s are produced from [[catechols]] and [[hydroquinone]]s and even [[nitroalkane]]s are oxidized.<ref>{{cite journal |doi=10.1021/cr068408n|title=Cerium(IV) Ammonium NitrateA Versatile Single-Electron Oxidant |year=2007 |last1=Nair |first1=Vijay |last2=Deepthi |first2=Ani |journal=Chemical Reviews |volume=107 |issue=5 |pages=1862–1891 |pmid=17432919 }}</ref><ref>{{cite journal |doi=10.1021/cr100004p|title=Cerium(IV) Ammonium Nitrate as a Catalyst in Organic Synthesis |year=2010 |last1=Sridharan |first1=Vellaisamy |last2=Menéndez |first2=J. Carlos |journal=Chemical Reviews |volume=110 |issue=6 |pages=3805–3849 |pmid=20359233 }}</ref>

CAN provides an alternative to the [[Nef reaction]]; for example, for [[ketomacrolide]] synthesis where complicating side reactions usually encountered using other reagents. Oxidative halogenation can be promoted by CAN as an ''in situ'' oxidant for benzylic bromination, and the iodination of ketones and [[uracil]] derivatives.

===For the synthesis of heterocycles===
Catalytic amounts of aqueous CAN allow the efficient synthesis of [[quinoxaline]] derivatives. Quinoxalines are known for their applications as dyes, [[organic semiconductor]]s, and DNA cleaving agents. These derivatives are also components in antibiotics such as [[echinomycin]] and [[actinomycin]]. The CAN-catalyzed three-component reaction between [[aniline]]s and [[alkyl vinyl ether]]s provides an efficient entry into 2-methyl-1,2,3,4-tetrahydroquinolines and the corresponding [[quinoline]]s obtained by their [[aromatization]].

===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}}