Synlett 2013; 24(1): 137-138
DOI: 10.1055/s-0032-1317531
spotlight
© Georg Thieme Verlag Stuttgart · New York

Manganese(III) Acetate

Manoj Mondal
Department of Chemistry, Dibrugarh University, Dibrugarh 786004, India   Email: manojjmondal@gmail.com
› Author Affiliations
Further Information

Publication History

Publication Date:
04 December 2012 (online)

Dedicated to my honourable mentor Dr. Utpal Bora

Introduction

Manganese(III) acetate [Mn(OAc)3]-mediated free-radical reactions have emerged as important synthetic methods. Manganese acetate can be used as an oxidizing and chlorinating agent[ 1 ] and in some cases in alkylations[ 1 ] and inter- and intramolecular cyclizations.[ 2 ] Due to the poor solubility of Mn(OAc)3 in common organic solvents, Mn(OAc)3-mediated reactions are often carried out in acetic acid, although other solvents including toluene, alcohols, acetonitrile, dichloromethane and chlorobenzene can be used.[ 3 ] Mn(OAc)3 promotes the synthesis of many alkaloids,[ 4 ] triterpenes,[ 5 ] and drugs.[ 6 ] Mn(OAc)3 is commercially available in form of its dehydrate as a brown powder and can be prepared in the laboratory[ 7 ] by adding KMnO4 to a pre-heated mixture of Mn(OAc)2 and glacial acetic acid (Scheme [1]). Addition of acetic anhydride to the reaction produces the anhydrous form.[ 8 ]

Zoom Image
Scheme 1 Preparation of manganese (III) acetate
 
  • References

  • 1 Pan X.-Q, Zou J.-P, Zhang W. Mol. Divers. 2009; 13: 421
    • 3a Wang GW, Dong YW, Wu P, Yuan TT, Shen YB. J. Org. Chem. 2008; 73: 7088
    • 3b Snider BB. Chem. Rev. 1996; 96: 339
    • 4a Wang X, Ma Z, Lu J, Tan X, Chen C. J. Am. Chem. Soc. 2011; 133: 15350
    • 4b Cong Z, Miki T, Urakawa O, Nishino H. J. Org. Chem. 2009; 74: 3978
    • 4c Tsubusaki T, Nishino H. Tetrahedron 2009; 65: 9448
  • 5 Demir AS, Gross RS, Dunlap NK, Hashemi AB, Watt DS. Tetrahedron Lett. 1986; 27: 5567
  • 6 Xu W, Zou J.-P, Zhang W. Tetrahedron Lett. 2010; 51: 2639
  • 7 Heiba EI, Dessau RM, Kolhl Jr. WJ. J. Am. Chem. Soc. 1969; 91: 138
  • 8 Snider BB. Manganese(III) Acetate. In Encyclopedia of Reagents for Organic Synthesis. 2001. DOI: 10 1002/047084289X.rm018
  • 9 Haque MA, Nishino H. Synth. Commun. 2012; 42: 608
    • 10a Demir AS, Findik H, Saygili N, Subasi NT. Tetrahedron 2010; 66: 1308
    • 10b Demir AS, Reis O, Emrullahoglu M. J. Org. Chem. 2003; 68: 578
    • 10c Demir AS, Reis O, Karaaslan EO. J. Chem. Soc., Perkin Trans. 1 2001; 3042
  • 11 Gowda S, Rai KM. L. J. Mol. Cat. A: Chem. 2004; 217: 27
  • 12 Demir AS, Tanyeli C, Altinel E. Tetrahedron Lett. 1997; 38: 7267
  • 13 Haque MA, Nishino H. Heterocycles 2011; 83: 1783
  • 14 Sharma GV. M, Lavanya B, Mahalingam AK, Krishna PR. Tetrahedron Lett. 2000; 41: 10323
  • 15 Pan X.-Q, Zou J.-P, Zhang G.-L, Zhang W. Chem. Commun. 2010; 46: 1721