Synlett 2006(15): 2513-2514  
DOI: 10.1055/s-2006-949628
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Sodium Perborate (SPB)

Maliheh Safaiee*
Department of Chemistry, Bu-Ali Sina University, Hamadan Zip Code 6517838683, Iran
e-Mail: msafaiee@basu.ac.ir;

Further Information

Publication History

Publication Date:
08 September 2006 (online)

Biographical Sketches

Maliheh Safaiee was born in Saveh, Iran in 1976. She received her B.Sc. in chemistry from the Bu-Ali Sina University, Iran and her M.Sc. in organic chemistry from the same university under the guidance of Prof. M. A. Zolfigol. She is currently working towards her Ph.D. under the supervision of Professor D. Habibi at Bu-Ali Sina University. Her research interests include the development of new organic methodology.

Introduction

Sodium perborate (SPB) has the empirical formula NaBO3·xH2O. Two commercially available forms correspond stoichiometrically to x = 1 or 4, and are known as the monohydrate and tetrahydrate. [1]

SPB was shown in 1961 to be the disodium salt of 1,4-di­boratetroxane dianion (1). Hence, the monohydrate ­actually corresponds to the anhydrous salt, and the ­tetrahydrate to a hexahydrated form of it. SPB is a con­venient source of H2O2, the borate helping somewhat to buffer, stabilize against decomposition, and activate ­towards nucleophilic oxidations, through associated ­species such as [B(OH)3(OOH)]-. [2]

Sodium perborate is a cheap, stable, non-toxic oxidizing agent, easily handled, crystalline, easily available peroxygen compound and has industrial application. [3]

Sodium perborate has been used for a variety of oxidation reactions. This reagent can be applied to the synthesis of amides from nitriles, [4] quinazoline-4-(3H)-ones from o-amido benzonitriles, [5] sulfoxides from sulfides, [6] esters from cyclic acetals, [7] carbonyl compounds from oximes, [8] aldehydes from terminal alkenes, [9] the synthesis of aryl thiocyanates [10] and Corey aldehyde, [11] and transesterification of β-keto esters. [12]

Abstracts

(A) Sodium perborate has been employed as an efficient catalyst for the preparation of (diacetoxyiodo)arenes from iodoarenes. [13]

(B) Bjorsvik et al. reported a new catalytic oxidation method for the preparation of aromatic carboxylic acids from methyl aryl ­ketones. The catalytic cycle is based on the use of an electron-­deficient nitroarene as a catalyst with either one of the two cheap and green oxidants sodium perborate or sodium percarbonate. [14]

(C) Several primary aromatic amines, substituted with electron-­donating groups, were converted into their corresponding nitro ­compounds in good to excellent yield with sodium perborate ­tetrahydrate (SPB) in micellar media in the presence of a catalytic amount of tungstophosphoric acid (H3PW·nH2O). [15]

(D) Roche et al. reported the selective monobromination of various deactivated anilines using potassium bromide and sodium perborate. The use of ammonium molybdate as catalyst accelerates the rate of reaction but is not essential to obtain good yields and high selectivities. [16]

(E) Decarbonylation of β-aryl and β-heterocycle pyruvic acids ­catalyzed by sodium perborate tetrahydrate in aqueous solution at ambient temperature give the corresponding arylacetic acids in good yield. [17] [18]

(F) Bandgar et al. show unique selectivity and constitute a useful alternative to commonly accepted deacylation procedures. Moreover, the superiority and flexibility of the protocol lies in its ease of operation and simplicity in work-up which involves mere filtration of the reagent. Clean deprotection under mild and neutral ­conditions using this cheap and easily available reagent make this simple protocol economically attractive. [19]

(G) Rearrangement of aldimine to formamide is another appli­cation of sodium perborate. C,N-Diarylaldimines and C-alkyl-N-arylaldimines undergo this rearrangement. [20]

    References

  • 1 McKillop A. Sanderson WR. Tetrahedron  1995,  51:  6145 
  • 2 McKillop A. Sanderson WR. J. Chem. Soc., Perkin Trans. 1  2000,  471 
  • 3 Mandare PN. Pangarkar VG. Chem. Eng. Sci.  2003,  58:  1125 
  • 4 Sharifi A. Mohesenzadeh F. Mojtahedi MM. Saidi MR. Balalaie S. Synth. Commun.  2001,  31:  431 
  • 5 Baudoin B. Ribeill Y. Vicker N. Synth. Commun.  1993,  23:  2833 
  • 6 Bower JF. Martin CJ. Rawson DJ. Slawin AMZ. Williams JMJ. J. Chem. Soc., Perkin Trans. 1  1995,  333 
  • 7 Bhat S. Ramesha AR. Chandrasekaran S. Synlett  1995,  329 
  • 8 Bandgar BP. Shaikh SI. Iyer S. Synth. Commun.  1996,  26:  1163 
  • 9 Kabalka GW. Yu S. Li N.-S. Tetrahedron Lett.  1997,  38:  7681 
  • 10 Jadhav VK. Pal RR. Wadgaonkar PP. Salunkhe MM. Synth. Commun.  2001,  31:  3041 
  • 11 Espiritu M. Handley PN. Neumann R. Adv. Synth. Catal.  2003,  345:  325 
  • 12 Bandgar BP. Sadavarte VS. Uppalla LS. Chem. Lett.  2001,  894 
  • 13 DelwarHossain Md. Kitamura T. J. Org. Chem.  2005,  70:  6984 
  • 14 Bjorsvik H.-R. Merinero JAV. Liguori L. Tetrahedron Lett.  2004,  45:  8615 
  • 15 Firouzabadi H. Iranpoor N. Amani K. Green Chem.  2001,  3:  131 
  • 16 Roche D. Prasad K. Repic O. Blacklock TJ. Tetrahedron Lett.  2000,  41:  2083 
  • 17 Morrow N. Ramsden CA. Sargent BJ. Wallett CD. Tetrahedron  1998,  54:  9603 
  • 18 Ramsden CA. Sargent BJ. Wallett CD. Tetrahedron Lett.  1996,  37:  1901 
  • 19 Bandgar BP. Uppalla LS. Sadavarte VS. Patil SV. New J. Chem.  2002,  26:  1273 
  • 20 Nongkunsarn P. Ramsden CA. Tetrahedron  1997,  53:  3805 

    References

  • 1 McKillop A. Sanderson WR. Tetrahedron  1995,  51:  6145 
  • 2 McKillop A. Sanderson WR. J. Chem. Soc., Perkin Trans. 1  2000,  471 
  • 3 Mandare PN. Pangarkar VG. Chem. Eng. Sci.  2003,  58:  1125 
  • 4 Sharifi A. Mohesenzadeh F. Mojtahedi MM. Saidi MR. Balalaie S. Synth. Commun.  2001,  31:  431 
  • 5 Baudoin B. Ribeill Y. Vicker N. Synth. Commun.  1993,  23:  2833 
  • 6 Bower JF. Martin CJ. Rawson DJ. Slawin AMZ. Williams JMJ. J. Chem. Soc., Perkin Trans. 1  1995,  333 
  • 7 Bhat S. Ramesha AR. Chandrasekaran S. Synlett  1995,  329 
  • 8 Bandgar BP. Shaikh SI. Iyer S. Synth. Commun.  1996,  26:  1163 
  • 9 Kabalka GW. Yu S. Li N.-S. Tetrahedron Lett.  1997,  38:  7681 
  • 10 Jadhav VK. Pal RR. Wadgaonkar PP. Salunkhe MM. Synth. Commun.  2001,  31:  3041 
  • 11 Espiritu M. Handley PN. Neumann R. Adv. Synth. Catal.  2003,  345:  325 
  • 12 Bandgar BP. Sadavarte VS. Uppalla LS. Chem. Lett.  2001,  894 
  • 13 DelwarHossain Md. Kitamura T. J. Org. Chem.  2005,  70:  6984 
  • 14 Bjorsvik H.-R. Merinero JAV. Liguori L. Tetrahedron Lett.  2004,  45:  8615 
  • 15 Firouzabadi H. Iranpoor N. Amani K. Green Chem.  2001,  3:  131 
  • 16 Roche D. Prasad K. Repic O. Blacklock TJ. Tetrahedron Lett.  2000,  41:  2083 
  • 17 Morrow N. Ramsden CA. Sargent BJ. Wallett CD. Tetrahedron  1998,  54:  9603 
  • 18 Ramsden CA. Sargent BJ. Wallett CD. Tetrahedron Lett.  1996,  37:  1901 
  • 19 Bandgar BP. Uppalla LS. Sadavarte VS. Patil SV. New J. Chem.  2002,  26:  1273 
  • 20 Nongkunsarn P. Ramsden CA. Tetrahedron  1997,  53:  3805