Subscribe to RSS
DOI: 10.1055/s-2004-836028
Oxalic Acid: A Very Useful Brønsted Acid in Organic Synthesis
Publication History
Publication Date:
25 November 2004 (online)
![](https://www.thieme-connect.de/media/synlett/200415/lookinside/thumbnails/10.1055-s-2004-836028-1.jpg)
Introduction
The title compound oxalic acid is available in anhydrous and dihydrate forms and exhibits several features which have made it particularly attractive as a reagent in organic synthesis. Oxalic acid is a mild Brønsted acid, which finds application in the Beckmann reaction, [1] protection and deprotection of carbonyl compounds, [2-4] and various selective cleavage and hydrolytic reactions. It is frequently used as a mild acidic quench for a variety of reactions including oxidations. [5] Oxalic acid has also been used as an acidic agent in a number of condensation processes such as condensation of allylic alcohols with aromatic rings, [6] carbonyl compounds and hydrazines, [7] aromatic amines and aldehydes, [8] and it has been utilized as a bifunctional condensation partner in the synthesis of heterocyclic systems. [9]
Oxalic acid is the simplest of the dicarboxylic acids and is widely used in inorganic chemistry as a precipitant and chelating agent (oxalate as a bidentate ligand has been of great interest in coordination chemistry). [10]
- 1
Chandrasekhar S.Gopalaiah K. Tetrahedron Lett. 2003, 44: 7437 -
2a
Andersen NH.Uh H.-S. Synth. Commun. 1973, 3: 125 -
2b
Smith AB.Empfield JR.Vaccaro HA. Tetrahedron Lett. 1989, 30: 7325 -
2c
Caine D.Venkataramu SD.Kois A. J. Org. Chem. 1992, 57: 2960 -
2d
Ziegler FE.Becker MR. J. Org. Chem. 1990, 55: 2800 -
3a
Pearson WH.Poon Y.-F. Tetrahedron Lett. 1989, 30: 6661 -
3b
Mitani K.Yoshida T.Morikawa K.Iwanaga Y.Koshinaka E.Kato H.Ito Y. Chem. Pharm. Bull. 1988, 36: 367 -
3c
Huet F.Lechevallier A.Pellet M.Conia JM. Synthesis 1978, 63 -
4a
Martin VA.Murray DH.Pratt NE.Zhao Y.-b.Albizati KF. J. Am. Chem. Soc. 1990, 112: 6965 -
4b
Avery MA.Chong WKM.Detre G. Tetrahedron Lett. 1990, 31: 1799 -
5a
Apparao S.Schmidt RR. Synthesis 1987, 896 -
5b
Liu H.-J.Nyangulu JM. Synth. Commun. 1989, 19: 3407 - 6
Fieser LF. J. Am. Chem. Soc. 1939, 61: 3467 - 7
Paquette LA.Wang T.-Z.Vo NH. J. Am. Chem. Soc. 1993, 115: 1676 - 8
Peesapati V.Pauson PL.Pethrick RA. J. Chem. Res., Synop. 1987, 194 - 9
Eweiss NF.Bahajaj AA. J. Heterocycl. Chem. 1987, 24: 1173 -
10a
Krishnamurty KV.Harris GM. Chem. Rev. 1961, 61: 213 -
10b
Kim D.-J.Kroeger DM. J. Mater. Sci. 1993, 28: 4744 -
11a
Burn D.Petrow V. J. Chem. Soc. 1962, 364 -
11b
Weinstein B.Fenselau AH. J. Org. Chem. 1965, 30: 3209 - 12
Boeckman RK.Walters MA.Koyano H. Tetrahedron Lett. 1989, 30: 4787 -
13a
Demyttenaere J.Syngel KV.Markusse AP.Vervisch S.Debenedetti S.Kimpe ND. Tetrahedron 2002, 58: 2163 -
13b
Carlin RB.Constantine DA. J. Am. Chem. Soc. 1947, 69: 50 -
13c
Miller RE.Nord FF. J. Org. Chem. 1950, 15: 89 -
14a
Bartlett PA.Meadows JD.Ottow E. J. Am. Chem. Soc. 1984, 106: 5304 -
14b
Lygo B.O’Connor N. Tetrahedron Lett. 1987, 28: 3597 -
15a
Comins DL.Abdullah AH.Mantlo NB. Tetrahedron Lett. 1984, 25: 4867 -
15b
Comins DL.Hong H. J. Am. Chem. Soc. 1991, 113: 6672 - 16
Giles M.Hadley MS.Gallagher T. J. Chem. Soc., Chem. Commun. 1990, 1047