Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 43, 2013 - Issue 1
926
Views
10
CrossRef citations to date
0
Altmetric
Original Articles

SOCl2/β-Cyclodextrin: A New and Efficient Catalytic System for Beckmann Rearrangement and Dehydration of Aldoximes Under Aqueous Condition

&
Pages 118-128 | Received 03 Jan 2011, Published online: 05 Sep 2012

REFERENCES

  • Croig , D. ; Trost , B. M. ; Fleming , I. ; Ley , S. V. In Comprehensive Organic Synthesis ; Pergamon Press : Oxford , 1991 ; vol. 7 , pp. 689 – 702 .
  • (a) Gregory , B. J. ; Modooie , R. B. ; Schofield , K. Kinetics and mechanism of the Beckmann rearrangement of acetophenone oximes in sulphuric acid . J. Chem. Soc. B 1970 , 2 , 338 – 346 ; (b) Guy , A. ; Gutte , J. P. ; Long , G. Utilization of polyphosphoric acid in the presence of a co-solvent . Synthesis 1980 , 3 , 222 – 3 ; (c) Eaton , P. E. ; Carison , G. R. ; Lee , J. T. Phosphorus pentoxide–methanesulfonic acid: Convenient alternative to polyphosphoric acid . J. Org. Chem. 1973 , 38 , 4071 .
  • (a) Hashimoto , M. ; Obora , Y. ; Sakaguchi , S. ; Ishii , Y. Beckmann rearrangement of ketoximes to lactams by triphosphazene catalyst . J. Org. Chem. 2008 , 73 , 2894 ; (b) Li , D. ; Shi , F. ; Guo , S. ; Deng , Y. Highly efficient Beckmann rearrangement and dehydration of oximes . Tetrahedron Lett. 2005 , 46 , 671 ; (c) Ramalingan , C. ; Park , Y.-T. Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile . J. Org. Chem. 2007 , 72 , 4536 ; (d) Pi , H.-J. ; Dong , J.-D. ; An , N. ; Du , W. ; Deng , W.-P. Unexpected results from the re-investigation of the Beckmann rearrangement of ketoximes into amides by using TsCl . Tetrahedron 2009 , 65 , 7790 ; (e) Ronchin , L. ; Vavasori , A. On the mechanism of the organocatalyzed Beckmann rearrangement of cyclohexanone oxime by trifluoroacetic acid in aprotic solvent . J. Mol. Catal. A: Chem. 2009 , 313 , 22 .
  • (a) Iranpoor , N. ; Firouzabadi , H. ; Aghapour , G. A rapid and facile conversion of primary amides and aldoximes to nitriles and ketoximes to amides with triphenylphosphine and N-chlorosuccinamide . Synth. Commun. 2002 , 32 , 2535 ; (b) Antikumar , S. ; Chandrasekhar , S. Improved procedures for the Beckmann rearrangement: The reaction of ketoxime carbonates with boron trifluoride etherate . Tetrahedron Lett. 2000 , 41 , 5427 ; (c) Ren , R. X. ; Zueva , L. D. ; Ou , W. Formation of ϵ-caprolactam via catalytic Beckmann rearrangement using P2O5 in ionic liquids . Tetrahedron Lett. 2001 , 42 , 8441 .
  • (a) De Luca , L. ; Giacomelli , G. ; Porcheddu , A. Beckmann rearrangement of oximes under very mild conditions . J. Org. Chem. 2002 , 67 , 6272 ; (b) Arisawa , M. ; Yamaguchi , M. Rhodium-catalyzed Beckmann rearrangement . Org. Lett. 2001 , 3 , 311 ; (c) Boruah , M. ; Konwar , D. AlCl3 · 6H2O/KI/H2O/CH3CN: A new alternate system for dehydration of oximes and amides in hydrated media . J. Org. Chem. 2002 , 67 , 7138 ; (d) Furuya , Y. ; Ishihara , K. ; Yamamoto , H. Cyanuric chloride as a mild and active Beckmann rearrangement catalyst . J. Am. Chem. Soc. 2005 , 127 , 11240 ; (e) Yan , P. ; Batamack , P. ; Prakash , G. K. ; Olah , G. A. ; Gallium(III) triflate–catalysed Beckmann rearrangement . Catal. Lett. 2005 , 103 ( 3–4 ), 165 – 168 .
  • (a) Boero , M. ; Ikeshoji , T. ; Liew , C. C. ; Terakura , K. ; Parrinello , M. Hydrogen bond–driven chemical reactions: Beckmann rearrangement of cyclohexanone oxime into ϵ-caprolactam in supercritical water . J. Am. Chem. Soc. 2004 , 126 , 6280 ; (b) Ikushima , Y. ; Hatakeda , K. ; Sato , M. ; Sato , O. ; Arai , M. Innovation in a chemical reaction process using a supercritical water microreaction system: Environmentally friendly production of ϵ-caprolactam . Chem. Commun. 2002 , 19 , 2208 ; (c) Ikushima , Y. ; Hatakeda , K. ; Sato , O. ; Yokoyama , T. ; Arai , M. Noncatalytic organic synthesis using supercritical water: The peculiarity near the critical point . Angew. Chem. Int. Ed. 1999 , 38 , 2910 .
  • (a) Liu , X. ; Xiao , L. ; Wu , H. ; Li , Z. ; Chen , J. ; Xia , C. Novel acidic ionic liquids–mediated zinc chloride: Highly effective catalysts for the Beckmann rearrangement. Catal. Commun. 2009, 10, 424; (b) Yadav , L. D. S. ; Garima ; Srivastava , V. P. Bromodimethylsulfonium bromide (BDMS) in ionic liquid: A mild and efficient catalyst for Beckmann rearrangement. Tetrahedron Lett. 2010, 51, 739; (c) Guo , S. ; Du , Z. ; Zhang , S. ; Li , D. ; Li , Z. ; Deng , Y. Clean Beckmann rearrangement of cyclohexanone oxime in caprolactam-based Brønsted acidic ionic liquids. Green Chem. 2006, 8, 296; (d) Betti , C. ; Landini , D. ; Maia , A. ; Pasi , M. Beckmann rearrangement of oximes catalyzed by cyanuric chloride in ionic liquids. Synlett 2008, 908.
  • (a) Forni , L. ; Fornasari , G. ; Giordano , G. ; Lucarelli , C. ; Katovic , A. ; Trifiro , F. ; Perri , C. ; Nagy , J. B. Vapor-phase Beckmann rearrangement using high silica zeolite catalyst . Phys. Chem. Chem. Phys. 2004 , 6 , 1842 ; (b) Mao , D. ; Lu , G. ; Chen , Q. Vapor-phase Beckmann rearrangement of cyclohexanone oxime over B2O3/TiO2–ZrO2: The effect of catalyst calcination temperature and solvent . Appl. Catal. A 2005 , 279 , 145 ; (c) Dongare , M. K. ; Bhagwat , V. V. ; Ramana , C. V. ; Gurjar , M. K. Silica-supported MoO3: A mild heterogeneous catalyst for the Beckmann rearrangement and its application to some sugar-derived ketoximes . Tetrahedron Lett. 2004 , 45 , 4759 ; (d) Kim , S. J. ; Jung , K. D. ; Joo , O. S. ; Kim , E. J. ; Kang , T. B. Catalytic performance of metal oxide–loaded Ta-ilerite for vapor-phase Beckmann rearrangement of cyclohexanone oxime . Appl. Catal. A 2004 , 266 , 173 .
  • (a) Dinalar , G. ; Robert , H. C. Terpyridine ruthenium–catalysed one-pot conversion of aldehydes into amides . Organometallics 2009 , 28 , 922 – 924 ; (b) Lal Dhar , S. Y. ; Rajesh , P. ; Vishnu , P. S. Bromodimethylsulfonium–ZnCl2: A mild and efficient catalytic system for Beckmann rearrangement . Synthesis 2010 , 11 , 1771 – 1776 ; (c) Ruben , S. R. ; Johann , B. ; Silvia , D. G. ; Nicolas , M. ; Steven , P. N. Au/Ag-cocatalysed aldoximes to amides rearrangement under solvent- and acid-free condition . J. Org. Chem. 2010 , 75 , 1197 – 1202 ; (d) Chandrashekhar , S. ; Gopalaiah , K. T. Beckmann reaction of oximes catalysed by chloral: Mild and neutral procedures . Tetrahedron Lett. 2003 , 44 , 755 .
  • (a) Mona , H. S. ZnO/CH3COCl: A new and highly efficient catalyst for dehydration of aldoximes into nitrile under solvent-free condition . Synthesis 2005 , 5 , 787 – 790 ; (b) Goffredo , R. ; Graziano , B. ; Sandro , C. Nitriles from aldoximes: A new reaction of phoshonitrilic chloride . J. Org. Chem. 1973 , 38 , 1060 ; (c) Singh , M. K. ; Lakshman , M. K. A simple synthesis of nitriles from aldoximes . J. Org. Chem. 2009 , 74 , 3079 – 3084 ; (d) Yang , S. H. ; Chang , S. Highly efficient and catalytic conversion of aldoximes to nitriles . Org. Lett. 2001 , 3 , 4209 – 4211 ; (e) Kokare , N. D. ; Shinde , D. B. Efficient conversion of aldoximes to nitriles using phosphoric acid diethyl ester 2-phenylbenzimidazol-1-yl ester . Monatsh Chem. 2009 , 140 , 185 – 188 ; (f) Kiasat , A. R. ; Kazemi , F. Forough. Na2SO3/SOCl2, an efficient reagent for the dehydration of aldoximes to nitriles . Phosphorus, Sulfur Silicon. Relat. Elem. 2003 , 178 , 1377 ; (g) Kusurkar , R. S. ; Naik , N. H. ; Naik , P. N. Combination of AlCl3, ionic liquid and microwaves: An efficient method for dehydration and 1,3-dipolar cycloaddition: An unusual observation in presence of acrylonitrile . Synth. Commun. 2008 , 38 , 1952 ; (h) Rad , M. N. S. ; Nezhad , A. K. ; Behrouz , S. ; Amini , Z. ; Behrouz , M. Simple and highly efficient procedure for conversion of aldoximes to nitriles using N-(p-toluenesulfonyl) imidazole . Synth. Commun. 2010 , 2429 – 2440 ; (i) Kazemi , F. ; Kisat , A. R. ; Fadavipoor , E. A versatile method for the conversion of aldoximes to nitrile using silica gel/thionyl chloride . Phosphorus, Sulfur Silicon Relat. Elem. 2004 , 179 , 433 – 436 ; (j) Chaudhari , S. S. ; Akamanchi , K. G. Thionyl chloride–benztriozole: An efficient system for transformation of aldoximes to nitriles . Synth. Commun. 1999 , 29 , 1741 – 1745 ; (k) Tomami , B. ; Kiasat , A. R. Dehydration of aldoximes to nitrile using polymeric reagent . J. Chem. Res., Synop. 1999 , 444 – 445 ; (l) Kazemi , F. ; Kiasat , A. R. ; Javeherian , M. Improved and efficient conversion of nitriles using Na2CO3/SOCl2 . Ind. J. Chem. 2005 , 44B , 1954 – 1956 .
  • (a) Sosnovsky , G. ; Krough , J. A. A versatile method for the conversion of aldoximes to nitriles using selenium dioxide . Synthesis 1978 , 703 ; (b) Ho , T. L. ; Wong , C. M. Nitrile synthesis: The use of corey–kim system as dehydrant of aldoximes . Synth. Commun. 1975 , 5 , 423 ; (c) Dulcere , J. P. Vilsmeier reagent for a high-yield conversion of aldoximes to nitriles . Tetrahedron Lett. 1981 , 22 , 1599 .
  • (a) Kumar , P. V. ; Reddy , V. P. ; Shridhar , R. ; Srinivas , B. ; Narender , M. ; Rao , K. R. Supramolecular synthesis of 3-indolyl-3-hydroxy oxindoles under neutral conditions in water. J. Org. Chem. 2008, 73, 1646–1848; (b) Reddy , M. A. ; Bhanumathi , N. ; Rao , K. R. Asymmetric synthesis of 2-azido-1-arylethanols from azido aryl ketone-β-cyclodextrin complex and sodium borohydride in water. Chem. Commun. 2001, 1974–1975; (c) Narender , M. ; Reddy , M. S. ; Kumar , V. P. ; Srinivas , B. ; Shridhar , R. ; Nageswar , Y. V. D. ; Rao , K. R. Aqueous-phase one-pot synthesis of 2-aminothiazole or 2-aminoselenazole-5-carboxylate from β-keto ester, thiourea, or selenourea and N-bromosuccinamide under supramolecular catalyst. Synthesis 2007, 22, 3469–3472; (d) Murthy , S. N. ; Madhav , B. ; Kumar , A. V. ; Rao , K. R. ; Nageswar , Y. V. D. Facile and efficient synthesis of 3,4,5-substituted furan-2(5H)-ones by using β cyclodextrin as a reusable catalyst. Tetrahedron 2009, 65, 5251–5256.
  • Heng-Bing , J. ; Dong-Po , S. ; Ming , S. ; Zhong , L. ; Le-Fu , W. Transition-metal-free and substrate-selective oxidation of alcohols using water as an only solvent in the presence of β-cyclodextrin . Tetrahedron Lett. 2005 , 46 , 2517 .
  • (a) Kazuya , Y. ; Hiroshi , F. ; Yoshiyuki , O. ; Miyuki , K. ; Noritaka , M. A tungsten–tin mixed hydroxide as an efficient heterogeneous catalyst for dehydration of aldoximes to nitriles . Angew. Chem. Int. Ed. 2007 , 46 , 3922 ; (b) Sarvari , M. H. ZnO/CH3COCl: A new and highly efficient catalyst for dehydration of aldoximes into nitriles under solvent-free condition . Synthesis 2005 , 787 ; (c) Yan , P. ; Butamack , P. ; Prakash , G. ; Olah , G. Gallium(III) triflate–catalyzed dehydration of aldoximes . Catal. Lett. 2005 , 101 , 141 ; (d) Saini , A. ; Sanjy , K. ; Sandhu , J. S. Zinc-mediated facile and efficient dehydration of aldoximes to nitriles . Ind. J. Chem. 2005 , 44B , 1427 .
  • Handbook of Fine Chemicals; Aldrich: India, 2009.
  • Vogel's Textbook of Practical Organic Chemistry , , 5th ed. ; Pearson Education: London, 1989 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.