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DOI: 10.1055/s-0034-1379002
Silver(I) Oxide
Publication History
Publication Date:
08 September 2014 (online)
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Introduction
Silver(I) oxide (Ag2O) has been known for several centuries, and it is still widely used in synthetic chemistry, including in novel strategies. Ag2O is a black powder that is prepared by the reaction of aqueous silver nitrate and hydroxide salts (eq. 1, Scheme [1]).[1] However, thanks to its stability and low cost, organic chemists most frequently purchase it from commercial suppliers. This reagent has many applications: it can act as a base – due to the presence of oxide –, as an oxidant – due to its easy reduction to metallic silver –, as an halogen scavenger – due to the precipitation of silver halides –, or as a source of silver ion, particularly useful for organometallics preparation.
Ag2O is poorly soluble in all common solvents including water. It is however readily soluble in ammonia, leading the Tollens’ reagent[2] (eq. 2, Scheme [1]) which possesses a historical importance in the development of organic chemistry. This also illustrates the fact that (as for other metal-based reagents), properties of Ag2O may depend on the formation of complexes in the reaction medium.
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References
- 1 Janssen DE, Wilson CV. Org. Synth. 1956; 36: 46
- 2 Tollens B. Ber. Dtsch. Chem. Ges. 1882; 15: 1635
- 3 Bouzide A, Sauvé G. Org. Lett. 2002; 4: 2329
- 4 Wang H, She J, Zhang LH, Ye XS. J. Org. Chem. 2004; 69: 5774
- 5 Yu Z, Ma L, Yu W. Synlett 2010; 2607
- 6 Zhou H, Moberg C. J. Am. Chem.Soc. 2012; 134: 15992
-
7 Wang HM. J, Lin IJ. B. Organometallics 1998; 17: 972
- 8 Hayes J, Viciano M, Peris E, Ujaque G, Lledos A. Organometallics 2007; 26: 6170
- 9 Lin IJ.B, Vasam CS. Coord. Chem. Rev. 2007; 251: 642
- 10 N-Heterocyclic Carbenes: From Laboratory Curiosities to Efficient Synthetic Tools. Diez-Gonzales S. Royal Society of Chemistry; Cambridge: 2011
- 11 Naruta Y, Maruyama K , In Recent Advances in the Synthesis of Quinonoid Compounds, in: The Chemistry of the Quinonoid Compounds . Vol. 2, Part 1. Patai S, Rappoport Z. Wiley; Chichester, UK: 1988: 241
- 12 Hillard E, Vessières A, Thouin L, Jaouen G, Amatore C. Angew. Chem. 2006; 118: 291
- 13 Hamels D, Dansette PM, Hillard EA, Top S, Vessières A, Herson P, Jaouen G, Mansuy D. Angew. Chem. Int. Ed. 2009; 48: 9124
- 14 Maricich TJ, Allan MJ, Kislin BS, Chen AI. T, Meng FC, Bradord C, Kuan NC, Wood J, Aisagbonhi O, Poste A, Wride D, Kim S, Santos T, Fimbres M, Choi D, Elia H, Kaladjian J, Abou-Zahr A, Mejia A. Synthesis 2013; 45: 3361