Green Synthesis of Tetraalkylammonium Tribromide using Cerium(IV) Ammonium Nitrate (CAN) as Oxidant

References

• Gopinath , R. and Patel , B. K. 2000 . Tetrabutylammonium tribromide (TBATB)–MeOH: An efficient chemoselective reagent for the cleavage of tert‐butyldimethylsilyl (TBDMS) ethers . Org. Lett. , 2 ( 26 ) : 4177
   PubMed Web of Science ®Google Scholar
• Gopinath , R. , Haque , S. J. and Patel , B. K. 2002 . Tetrabutylammonium tribromide (TBATB) as an efficient generator of HBr for an efficient chemoselective reagent for acetalization of carbonyl compounds . J. Org. Chem. , 67 : 5842
   PubMed Web of Science ®Google Scholar
• Naili , S. , Gopinath , R. , Goswami , M. and Patel , B. K. 2004 . Chemoselective thioacetalisation and transthioacetalisation of carbonyl compounds catalysed by tetrabutylammonium tribromide (TBATB) . Org. Biomol. Chem. , 2 ( 11 ) : 1670
   Web of Science ®Google Scholar
• Taylor , R. 1990 . Electrophilic Aromatic Substitution New York : Wiley .
   Google Scholar
• Fuson , R. C. 1962 . Reaction of Organic Compounds 58; 98 New York : Wiley .
   Google Scholar
• Normal , R. O. C. and Taylor , R. 1965 . Electrophilic Substitution in Benzenoid Compounds 130 New York : Elsevier .
   Google Scholar
• Fieser , L. F. and Fieser , M. 1967 . Reagents for Organic Synthesis 967 Wiley: New York .
   Google Scholar
• Avramoff , M. , Weiss , J. and Schaechter , O. 1963 . The brominating properties of tetramethylammonium tribromide . J. Org. Chem. , 28 : 3256
   Web of Science ®Google Scholar
• Kajigneshi , S. , Kakinami , T. , Tokiyama , H. , Hirakawa , T. and Okamoto , T. 1987 . Bromination of phenols by use of benzyltrimethylammonium tribromide . Chem. Lett. , : 627
   Google Scholar
• Muathen , H. A. 1992 . 1,8‐Diazableyelo[5.4.0]undec‐7‐ene hydrobromide perbromide: A new mild stable brominating agent for aromatic compounds . J. Org. Chem. , 57 : 2740
   Web of Science ®Google Scholar
• Buckles , R. E. , Popov , A. I. , Zelezny , W. F. and Smith , R. J. 1951 . Spectrophotometric study of tetrabutylammonium tribromide . J. Am. Chem. Soc. , 73 : 4525
   Web of Science ®Google Scholar
• Chaudhuri , M. K. , Khan , A. T. , Patel , B. K. , Dey , D. , Kharmawophlang , W. , Lakshmiprabha , T. R. and Mandal , G. C. 1998 . An environmentally benign synthesis of organic ammonium tribromides (OATB) and bromination of selected organic substrates by tetrabutylammonium tribromide (TBATB) . Tetrahedron Lett. , 39 : 8163
   Web of Science ®Google Scholar
• Sarmah , S. , Kalita , D. , Hazarika , P. , Borah , R. and Islam , N. S. 2004 . Synthesis of newer dinuclear and mono‐nuclear peroxo‐vanadium complexes containing biogenic co‐ligands: A comparative study of some of their parameters . Polyhedron , 23 : 1097
   Web of Science ®Google Scholar
• De Klein , W. J. Organic Synthesis by Oxidation with Metal Compounds Edited by: Mijs , W. J. and de Jonge , C. R.H. 261
   Google Scholar
• Ho , T. L. 1973 . Ceric ion oxidation in organic chemistry . Synthesis , : 347
   Web of Science ®Google Scholar
• Molander , G. A. 1992 . Chem. Rev. , 92 : 29
   Web of Science ®Google Scholar
• For review on CAN-mediated reactions, see Imamoto , T. 1994 . Lanthanide Reagents in Organic Synthesis 119 London : Academic Press .
   Google Scholar
• Allen , G. D. , Buzze , M. C.; Villagrán C. , Hardacre , C. and Compton , G. R. 2005 . A mechanistic study of the electro‐oxidation of bromide in acetonitrile and the room temperature ionic liquid, 1‐butyl‐3‐methylimidazolium bis(trifluoromethylsulfonyl) imide at platinum electrodes . J. Electroanl. Chem. , 575 : 311
   Web of Science ®Google Scholar
• Ershov , B. G. , Gordeev , A. V. , Janata , E. and Kelm , M. 2001 . Radiation–chemical oxidation of bromide ions and formation of tribromide ions in weakly acidic aqueous solutions . Mendeleev Commun. , 11 : 149
   Google Scholar
• Bora , U. , Chaudhuri , M. K. , Dey , D. and Dhar , S. S. 2001 . Peroxometal‐mediated environmentally favorable route to brominating agents and protocols for bromination of organics . Pure Appl. Chem. , 73 ( 1 ) : 93
   Web of Science ®Google Scholar
• Bellucci , G. , Bianchini , R. , Chiappe , C. and Ambrosetti , R. 1989 . Formation of pentabromide ions from bromine and bromide in moderate‐polarity aprotic solvents and their possible involvement in the product‐determining step of olefin bromination . J. Am. Chem. Soc. , 111 : 199
   Google Scholar