Synthesis and Reactivity Studies of a New Reagent, Ethyltriphenylphosphonium Tribromide

REFERENCES

• (a) Ma , K. ; Li , S. ; Weiss , R. G. Stereoselective bromination reactions using tridecylmethylphosphonium tribromide in a “stacked” reactor . Org. Lett. 2008 , 10 , 4155 – 4158 ; (b) Hajipour , A. R. ; Pourmousavi , S. A. ; Ruoho , A. E. Benzyltriphenylphosphonium tribromide: A mild, regenerable, and efficient reagent for the deprotection of dithioacetals . J. Sulfur Chem. 2004 , 25 , 401 – 405 ; (c) Hajipour , A. R. ; Pourmousavi , S. A. ; Ruoho , A. E. Simple and facile tetrahydropyranylation of alcohols by use of catalytic amounts of benzyltriphenylphosphonium tribromide . Synth. Commun. 2005 , 35 , 2889 – 2894 ; (d) Hajipour , A. R. ; Mallakpour , S. E. ; Imanieh , H. ; Pourmousavi , S. A. A controlled and selective bromination of phenols by benzyltriphenylphosphonium tribromide . J. Chem. Res. Synop. 2002 , 272 – 275 .
   PubMed Web of Science ®Google Scholar
• (a) Kavala , V. ; Naik , S. ; Patel , B. K. A new recyclable ditribromide reagent for efficient bromination under solvent-free condition . J. Org. Chem. 2005 , 70 , 4267 – 4271 ; (b) Jordan , A. D. ; Luo , C. ; Reitz , A. B. Efficient conversion of substituted aryl thioureas to 2-aminobenzothiazoles using benzyltrimethylammonium tribromide . J. Org. Chem. 2003 , 68 , 8693 – 8696 ; (c) Chiappe , C. ; Leandri , E. ; Pieraccini , D. Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromide as reagent/solvent . J. Chem. Soc., Chem. Commun. 2004 , 2536 – 2537 ; (d) Lee , J. C. ; Park , J. Y. ; Yoon , S. ; Bae , Y. Y. H. ; Lee , S. J. Efficient microwave induced direct α -halogenation of carbonyl compounds . Tetrahedron Lett. 2004 , 45 , 191 – 193 ; (e) Singhal , S. ; Jain , S. L. ; Sain , B. A simple and improved regioselective bromination of aromatic compounds using N-methylpyrrolidin-2-one hydrotribromide and aqueous hydrogen peroxide under mild reaction conditions . J. Mol. Catal. A: Chem. 2006 , 258 , 198 – 202 ; (f) Salazar , J. ; Dorta , R. Pentylpyridinium tribromide: A vapor pressure–free room-temperature ionic liquid analogue of bromine . Synlett 2004 , 1318 – 1320 ; (g) Naik , S. ; Kavala , V. ; Gopinath , R. ; Patel , B. K. Tetrabutylammonium tribromide–mediated condensation of carboxylic acids with alcohols . Arkivoc 2006 , 1 , 119 – 127 ; (h) Gosain , J. ; Sharma , P. K. Kinetics and mechanism of the oxidation of some vicinal and nonvicinal diols by tetrabutylammoniumtribromide . Proc. Indian Acad. Sci. (Chem. Sci.) 2003 , 115 , 135 ; (i) Kavala , V. ; Patel , B. K. Reinvestigation of mechanism of gem-diacylation chemoselective conversion of aldehydes to various gem-diacylates and their cleavage under acidic and basic conditions . Eur. J. Org. Chem. 2005 , 441 – 451 ; (j) Figueira , V. B. C. Tetra-n-butilammonium tribromide . Synlett 2006 , 2681 – 2682 ; (k) Alimenla , B. ; Kumar , A. ; Jamir , L. ; Sinha , D. ; Sinha , U. B. Microwave-induced reactions: An alternative route for chemical synthesis . Rad. Eff. Def. Sol. 2006 , 161 , 687 – 693 ; (l) Alimenla , B. ; Kumar , A. ; Jamir , L. ; Sinha , D. ; Sinha , U. B. An efficient microwave-induced solvent-free organic bromination using tetrabutylammonium tribromide . Acta Chim. Slov. 2009 , 56 , 457 – 461 .
   PubMed Web of Science ®Google Scholar
• (a) Cristau , H. J. ; Torreilles , E. ; Morand , P. ; Cristol , H. Phosphonium tribromides: Brominating agents for organic substrates. Phosphorus, Sulfur. Relat. Elem. 1985, 25, 357–367; (b) Armstrong , V. W. ; Chishti , N. H. ; Ramage , R. New brominating reagent: 2-Carboxyethyltriphenylphosphonium perbromide. Tetrahedron Lett. 1975, 6, 373–376.
   Web of Science ®Google Scholar
• (a) CCDC-627535 contain the supplementary crystallographic data for this article. This data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request.cif. Crystallographic description of ETPPTB (Fig 1): Crystal dimension (mm), 0.50 × 0.28 × 0.18, C20H20Br3P, Mr = 531.06; monoclinic, space group P2(1)/n; a = 10.1571(3) Å, b = 12.2399(3) Å, c = 16.9416(5) Å, α = γ = 90°, β = 90.678(2)°, V = 2106.06(10) Å3, Z = 4, ρcal = 1.675 Mg/m3; reflections collected = 18784; refinement method = full-matrix least-squares on F2; final R indices [I > 2sigma(I)] R1 = 0.0409, wR2 = 0.0924; R indices (all data) R1 = 0.0856, wR2 = 0.1089; goodness of fit = 1.005 .
   Google Scholar
• Buckingham , J. ; McDonald , F. (eds.) . Dictionary of Organic Compounds, , 6th ed. ; Chapman & Hall : London , 1996 .
   Google Scholar
• (a) Larock , R. C. Comprehensive Organic Transformations ; VCH : New York , 1989 ; (b) Otera , J. Esterification: Methods, Reactions, and Applications ; Wiley-VCH : Weinheim , 2003 .
   Google Scholar
• (a) Muhkerjee , A. K. ; Ashare , R. Isothiocyanates in the chemistry of heterocycles . Chem. Rev. 1991 , 91 , 1 – 24 ; (b) Stephensen , H. ; Zaragosa , F. Resin-bound isothiocyanates and their synthetic equivalents as intermediates for the solid-phase synthesis of substituted thiophenes . J. Org. Chem. 1997 , 62 , 6096 – 6097 ; (c) Al-Hourani , B. J. ; Banert , K. ; Gomaa , N. ; Vrobel , K. Synthesis of functionalized thiazoles via attack of heterocyclic nucleophiles on allenyl isothiocyanates . Tetrahedron 2008 , 64 , 5590 – 5597 ; (d) Fajkusova , D. ; Pazdera , P. Unexpected formation of benzothiazoles in the synthesis of new heterocycles: Benzo-1,2,4-dithiazines . Synthesis 2008 , 1297 – 1305 ; (e) Wu , Y.-J. ; Zhang , Y. An efficient one-pot synthesis of 3-substituted-5-amino-1,2,4-thiadiazoles from isothiocyanates and amidines . Tetrahedron Lett. 2008 , 49 , 2869 – 2871 ; (f) Thiel , O. R. ; Bernard , C. ; King , T. ; Dilmeghani-Serna , M. ; Bostick , T. ; Larson , R. D. ; Faul , M. M. Practical synthesis of a vanilloid receptor-1 antagonist . J. Org. Chem. 2008 , 73 , 3508 – 3515 .
   Google Scholar
• Nastruzzi , C. ; Cotesi , R. ; Eaposito , E. ; Menegatti , E. ; Leoni , O. ; Iori , R. ; Palmier , S. In vitro antiproliferative activity of isothiocyanates and nitriles generated by myrosinase-mediated hydrolysis of glucosinolates from seeds of cruciferous vegetables . J. Agric. Food. Chem. 2000 , 48 , 3572 – 3575 .
   PubMed Web of Science ®Google Scholar
• Xu , K. ; Thornalley , P. Studies on the mechanism of the inhibition of human leukaemia cell growth by dietary isothiocyanates and their cysteine adducts in vitro . J. Biochem. Pharmacol. 2000 , 60 , 221 – 231 .
   PubMed Web of Science ®Google Scholar
• (a) Boas , U. ; Jakobsen , M. H. A new synthesis of aliphatic isothiocyanates from primary amines, convenient for in situ use . J. Chem. Soc., Chem. Commun. 1995 , 1995 – 1996 ; (b) Boas , U. ; Pedersen , B. ; Christensen , J. B. Tetramethylfluoroformamidinium hexafluorophoshate—An improved synthesis and some new uses . Synth. Commun. 1998 , 28 , 1223 – 1231 ; (c) Boas , U. ; Pedersen , H. G. ; Christensen , J. B. ; Heegaard , P. M. H. Facile synthesis of aliphatic isothiocyanates and thioureas on solid phase using peptide coupling reagents . Tetrahedron Lett. 2004 , 45 , 269 – 272 .
   Google Scholar
• Dyer , E. ; Johnson , T. B. Nitro- and aminotriphenylguanidines . J. Am. Chem. Soc. 1932 , 54 , 777 – 787 .
   Google Scholar
• Hodgkins , J. E. ; Reeves , W. P. The modified Kaluza synthesis, III: The synthesis of some aromatic isothiocyanates . J. Org. Chem. 1964 , 29 , 3098 – 3099 .
   Web of Science ®Google Scholar
• Mesheram , H. M. ; Dale , S. ; Yadav , J. S. A general synthesis of isothiocyanates from dithiocarbamates using Claycop . Tetrahedron Lett. 1997 , 38 , 8743 – 8744 .
   Web of Science ®Google Scholar
• (a) Li , G. ; Tajima , H. ; Ohtani , T. An improved procedure for the preparation of isothiocyanates from primary amines by using hydrogen peroxide as the dehydrosulfurization reagent. J. Org. Chem. 1997, 62, 4539–4540; (b) Wang , R. ; Dolman , S. J. Isothiocyanates from tosyl chloride–mediated decomposition of in situ–generated dithiocarbamic acid salts. J. Org. Chem. 2007, 72, 3969–3971.
   PubMed Web of Science ®Google Scholar
• Nath , J. ; Ghosh , H. ; Yella , R. ; Patel , B. K. Molecular iodine–mediated preparation of isothiocyanates from dithiocarbamic acid salts . Eur. J. Org. Chem. 2009 , 1849 – 1851 .
   Google Scholar