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Synthesis 2012(2): 316-322
DOI: 10.1055/s-0031-1289628
DOI: 10.1055/s-0031-1289628
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkSynthesis of Sulfonyl Chlorides and Sulfonic Acids in SDS Micelles
Further Information
Received
21 September 2011
Publication Date:
30 November 2011 (online)
Publication History
Publication Date:
30 November 2011 (online)

Abstract
H2O2/POCl3 is found to be a reactive reagent system that can be used in sodium dodecyl sulfate (SDS) micellar solution in aqueous media for the direct oxidative chlorination of thiol and disulfide derivatives to give the desired sulfonyl chlorides. The oxidation of thiols and disulfides to sulfonic acids with this system is also reported. In most cases, these reactions are highly selective, simple, and clean, affording products in excellent yields and high purity.
Key words
micelles - oxidation - hydrogen peroxide - thiols - solvent systems - amphiphiles
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- Supporting Information (PDF)
- 1
Anastas P.Warner J. Green Chemistry: Theory and Practice Oxford University Press; New York: 1998.Reference Ris Wihthout Link - 2a
Tanaka K. The Chemistry of Sulfonic Acids, Esters and their Derivatives, In The Chemistry of Functional GroupsPatai S.Rapport Z. John Wiley & Sons; New York: 1991. Chap. 11. p.401Reference Ris Wihthout Link - 2b
Moore JD.Herpel RH.Lichtsinn JR.Flynn DL.Hanson PR. Org. Lett. 2003, 5: 105Reference Ris Wihthout Link - 2c
Dubbaka SR.Vogel P. J. Am. Chem. Soc. 2003, 125: 15292Reference Ris Wihthout Link - 2d
Kværno L.Werder M.Hauser H.Carreira EM. Org. Lett. 2005, 7: 1145Reference Ris Wihthout Link - 2e
Lassalle G,Galtier D, andGalli F. inventors; European Patent 643047.Reference Ris Wihthout Link - 2f
Lezina OM,Kuchin AV, andRubtsova SA. inventors; Russian Patent; 2289574.Reference Ris Wihthout Link - 3a
Bossard HH.Mory R.Schmid M.Zollinger H. Helv. Chim. Acta 1959, 42: 1653Reference Ris Wihthout Link - 3b
Albright JD.Benz E.Lanzilotti AE.Goldman L. Chem. Commun. 1965, 413Reference Ris Wihthout Link - 3c
Barco A.Benetti S.Pollini P.Tadia R. Synthesis 1974, 877Reference Ris Wihthout Link - 4a
Gareau Y.Pellicelli J.Laliberte S.Gauvreau D. Tetrahedron Lett. 2003, 44: 7821Reference Ris Wihthout Link - 4b
Norris T. J. Chem. Soc., Perkin Trans. 1 1978, 1378Reference Ris Wihthout Link - 4c
Barbero M.Bazzi S.Cadamuro S.Dughera S.Magistris C.Venturello P. Synlett 2010, 1803Reference Ris Wihthout Link - 5a
Blotny G. Tetrahedron Lett. 2003, 44: 1499Reference Ris Wihthout Link - 5b
Fujita S. Synthesis 1982, 423Reference Ris Wihthout Link - 6a
Meinzer A.Breckel A.Thaher BA.Manicone N.Otto H.-H. Helv. Chim. Acta 2004, 87: 90Reference Ris Wihthout Link - 6b
Barbero M.Cadamuro S.Degani I.Fochi R.Regondi V. Synthesis 1989, 957Reference Ris Wihthout Link - 7a
Nishiguchi A.Maeda K.Miki S. Synthesis 2006, 4131Reference Ris Wihthout Link - 7b
Bahrami K.Khodaei MM.Soheilizad M. Synlett 2009, 2773Reference Ris Wihthout Link - 8a
Prakash GKS.Mathew T.Panja C.Olah GA.
J. Org. Chem. 2007, 72: 5847Reference Ris Wihthout Link - 8b
Pu Y.-M.Christesen A.Ku Y.-Y. Tetrahedron Lett. 2010, 51: 418Reference Ris Wihthout Link - 9a
Organic Reactions in Water
Lindstrom UM. Blackwell Publishing; Oxford: 2007.Reference Ris Wihthout Link - 9b
Lindstrom UM. Chem. Rev. 2002, 102: 2751Reference Ris Wihthout Link - 9c
Blackmond DG.Armstrong A.Coombe V.Wells A. Angew. Chem. Int. Ed. 2007, 46: 3798Reference Ris Wihthout Link - 10a
Fendler JH.Fendler EJ. Catalysis in Micellar and Macromolecular Systems Academic Press; London: 1975.Reference Ris Wihthout Link - 10b
Mixed
Surfactant Systems
Holland PM.Rubingh DN. American Chemical Society; Washington DC: 1992.Reference Ris Wihthout Link - 10c
Structure
and Reactivity in Aqueous Solution
Cramer CJ.Truhlar DG. American Chemical Society; Washington DC: 1994.Reference Ris Wihthout Link - 10d
Surfactant-Enhanced Subsurface Remediation
Sabatini DA.Knox RC.Harwell JH. American Chemical Society; Washington DC: 1994.Reference Ris Wihthout Link - 11a
Lin HP.Mou CY.Lin SB. Adv. Mater. 2000, 12: 103Reference Ris Wihthout Link - 11b
Chan HBS.Budd PM.Naylor TV. J. Mater. Chem. 2001, 11: 951Reference Ris Wihthout Link - 11c
Gong X.Liu J.Baskaran S.Voise RD.Young JS. Chem. Mater. 2000, 12: 1049Reference Ris Wihthout Link - 11d
Chen CC.Chao CY.Lang ZH. Chem. Mater. 2000, 12: 1516Reference Ris Wihthout Link - 11e
Xiong Y.Xie Y.Yang J.Zhang R.Wu Ch.Du G. J. Mater. Chem. 2002, 12: 3712Reference Ris Wihthout Link - 12
Vriezema DM.Aragonés MC.Elemans JAAW.Cornelissen JJLM.Rowan AE.Nolte RJM. Chem. Rev. 2005, 105: 1445Reference Ris Wihthout Link - 13a
Noyori R.Aoki M.Sato K. Chem. Commun. 2003, 1977Reference Ris Wihthout Link - 13b
Noyori R. Chem. Commun. 2005, 1807Reference Ris Wihthout Link - 13c
Kaczorowska K.Kolarska Z.Mitka K.Kowalski P. Tetrahedron 2005, 61: 8315Reference Ris Wihthout Link - 14a
Greenwood NN.Earnshaw A. Chemistry of the Elements 2nd ed.: Butterworth-Heinemann; Oxford UK: 1997.Reference Ris Wihthout Link - 14b
Toy ADF. The Chemistry of Phosphorus Pergamon Press; Oxford UK: 1973.Reference Ris Wihthout Link - 14c
Elderfield RC. Heterocyclic Compounds Vol. 6: Wiley; New York: 1957. p.265-266Reference Ris Wihthout Link - 14d
Walker B. J. Organophosphorus Chemistry Penguin; Harmondsworth UK: 1972. p.101-116Reference Ris Wihthout Link - 15a
Bahrami K.Khodaei MM.Nejati A. Green Chem. 2010, 12: 1237Reference Ris Wihthout Link - 15b
Khodaei MM.Bahrami K.Farrokhi A. Synth. Commun. 2010, 40: 1492Reference Ris Wihthout Link - 16a
Manabe K.Mori Y.Kobayashi S. Tetrahedron 1999, 55: 11203Reference Ris Wihthout Link - 16b
Mori Y.Kakumoto K.Manabe K.Kobayashi S. Tetrahedron Lett. 2000, 41: 3107Reference Ris Wihthout Link - 16c
Kobayashi S.Wakabayashi T. Tetrahedron Lett. 1998, 39: 5389Reference Ris Wihthout Link - 16d
Manabe K.Kobaashi S. Tetrahedron Lett. 1999, 40: 3773Reference Ris Wihthout Link - 16e
Wang W.Wang SX.Qin X.-Y.Li JT. Synth. Commun. 2005, 35: 1263Reference Ris Wihthout Link - 16f
Gogoi P.Hazarika P.Konwar D. J. Org. Chem. 2005, 70: 1934Reference Ris Wihthout Link - 16g
Orsini F.Sello G.Fumagalli T. Synlett 2006, 1717Reference Ris Wihthout Link - 16h
Deb ML.Bhuyan PJ. Tetrahedron Lett. 2006, 47: 1441Reference Ris Wihthout Link - 16i
McKay CS.Kennedy DC.Pezacki JP. Tetrahedron Lett. 2009, 50: 1893Reference Ris Wihthout Link - 17
Hassan PA.Raghavan SR.Kaler EW. Langmuir 2002, 18: 2543Reference Ris Wihthout Link - 18a
Mukerjee P.Mysels KJ. Critical Micelle Concentration of Aqueous Surfactant Systems, NSRDS-NBS 36 U. S. Government Printing Office; Washington DC: 1971. p.107Reference Ris Wihthout Link - 18b
Rosen MJ. Surfactants and Interfacial Phenomena Wiley; New York: 1989. p.122-132Reference Ris Wihthout Link - 19
Bahrami K.Khodaei MM.Soheilizad M. J. Org. Chem. 2009, 74: 9287Reference Ris Wihthout Link - 20
Fries K.Eyelbertz E. Justus Liebigs Ann. Chem. 1915, 407: 194Reference Ris Wihthout Link - 21a
Langler RF.Marini ZA.Spalding ES. Can. J. Chem. 1979, 57: 3193Reference Ris Wihthout Link - 21b
March J. Advanced Organic Chemistry John Wiley & Sons; New York: 1985. p.1348Reference Ris Wihthout Link - 21c
Kim J.-G.Jang DO. Synlett 2010, 3049Reference Ris Wihthout Link - 21d
Soltani Rad MN.Khalafi-Nezhad A.Asrari Z.Behrouz S.Amini Z.Behrouz M. Synthesis 2009, 3983Reference Ris Wihthout Link - 22
Kalir A.Kalir HH. Biological Activity of Sulphonic Acid Derivatives, In Sulphonic Acids, Esters and Their DerivativesPatai S.Rappoport Z. Wiley; New York: 1991. Chap. 18. p.767-787Reference Ris Wihthout Link - 23a
Hoyle J. Preparation of Sulphonic Acids, Esters, Amides and Halides, In Sulphonic Acids, Esters and Their DerivativesPatai S.Rappoport Z. Wiley; New York: 1991. Chap. 10. p.351-399Reference Ris Wihthout Link - 23b
Capozzi G.Modena G. In The Chemistry of the Thiol GroupPatai S. Wiley; London: 1974. p.785-839Reference Ris Wihthout Link - 23c
Evans BJ.Doi JT.Musker K. J. Org. Chem. 1990, 55: 2337Reference Ris Wihthout Link - 24
Smith K.Hou D. J. Org. Chem. 1996, 61: 1530Reference Ris Wihthout Link - 25
Hajipour AR.Mirjalili BF.Zarei A.Khazdooz L.Ruoho AE. Tetrahedron Lett. 2004, 45: 6607Reference Ris Wihthout Link - 26
Shefer N.Carmeli M.Rozen S. Tetrahedron Lett. 2007, 48: 8178Reference Ris Wihthout Link - 27a
Bahrami K. Tetrahedron Lett. 2006, 47: 2009Reference Ris Wihthout Link - 27b
Khodaei MM.Bahrami K.Karimi A. Synthesis 2008, 1682Reference Ris Wihthout Link - 27c
Bahrami K.Khodaei MM.Kavianinia I. Synthesis 2007, 547Reference Ris Wihthout Link - 27d
Bahrami K.Khodaei MM.Naali F. J. Org. Chem. 2008, 73: 6835Reference Ris Wihthout Link - 27e
Bahrami K.Khodaei MM.Naali F. Synlett 2009, 569Reference Ris Wihthout Link - 27f
Bahrami K.Khodaei MM.Tirandaz Y. Synthesis 2009, 369Reference Ris Wihthout Link - 27g
Bahrami K.Khodaei MM.Soheilizad M. Tetrahedron Lett. 2010, 51: 4843Reference Ris Wihthout Link - 27h
Bahrami K.Khodaei MM.Sheikh Arabi M. J. Org. Chem. 2010, 75: 6208Reference Ris Wihthout Link - 27i
Bahrami K.Khodaei MM.Sheikh Arabi M. Tetrahedron Lett. 2010, 51: 6939Reference Ris Wihthout Link - 28a
Freeman F. Chem. Rev. 1984, 84: 117Reference Ris Wihthout Link - 28b
Oae S.Kim YH.Takara T.Fukushima D. Tetrahedron Lett. 1977, 1195Reference Ris Wihthout Link - 28c
Oae S.Takara T.Kim YH. Bull. Chem. Soc. Jpn. 1982, 55: 2484Reference Ris Wihthout Link - 28d
Oae S.Shinhama K.Fujimori K.Kim YH. Bull. Chem. Soc. Jpn. 1980, 53: 775Reference Ris Wihthout Link - 28e
Chau MM.Kice JL. J. Am. Chem. Soc. 1976, 98: 7711Reference Ris Wihthout Link - 29
Micheel VF.Weichbrodt K.Plenikowski J. Justus Liebigs Ann. Chem. 1953, 581: 238Reference Ris Wihthout Link - 30a
Ballistreri FP.Tomaselli GA.Toscano RM. Tetrahedron Lett. 2008, 49: 3291Reference Ris Wihthout Link - 30b
King JF.Slam M. Can. J. Chem. 1979, 57: 3278Reference Ris Wihthout Link - 30c
Everett JG. J. Chem. Soc. 1930, 2402Reference Ris Wihthout Link - 30d
Cavallini D.Federici G.Dupré S.Cannella C.Scandurra R. Pure Appl. Chem. 1979, 52: 147Reference Ris Wihthout Link - 31
Johnson WK. inventors; U. S. Patent 3311650.Reference Ris Wihthout Link - 32
Mohammadpoor-Baltork I.Memarian HR.Bahrami K. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179: 2315Reference Ris Wihthout Link