Ph₃P/I₂-Catalyzed Beckmann Rearrangement of Ketoximes into Amides

REFERENCES

• Smith , M. B. ; March , J. In Advanced Organic Chemistry, , 5th ed. ; John Wiley & Sons : New York , 2001 ; p. 1415. and references therein.
   Google Scholar
• Xia , C. G. ; Chen , J. ; Xiao , L. F. p-Toluenesulfonic acid–mediated zinc chloride: Highly effective catalyst for the Beckmann rearrangement . Tetrahedron Lett. 2007 , 48 , 7218 – 7221 .
   Web of Science ®Google Scholar
• Ghial , M. ; Abbaspur , A. ; Kalbasi , R. J. Vapor-phase Beckmann rearrangement of cyclohexanone oxime over H3PO4/ZrO2-TiO2 . Appl. Catal. A 2005 , 287 , 83 – 88 .
   Web of Science ®Google Scholar
• Formi , 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 – 1847 .
   Web of Science ®Google Scholar
• Mao , D. ; Lu , G. ; Chen , Q. 6-Aminocapronitrile as an alternative monomer for the nylon 6 synthesis . Appl. Catal. A: Gen. 2005 , 279 , 145 – 153 .
   Web of Science ®Google Scholar
• Mao , D. ; Chen , Q. ; Lu , G. Vapor-phase Beckmann rearrangement of cyclohexanone oxime over B2O3/TiO2- ZrO2 . Appl. Catal. A: Gen. 2003 , 244 , 273 – 282 .
   Web of Science ®Google Scholar
• Chandrasekhar , S. ; Gopalaiah , K. Ketones to amides via a formal Beckmann rearrangement in one pot: A solvent-free reaction promoted by anhydrous oxalic acid: Possible analogy with the Schmidt reaction . Tetrahedron Lett. 2003 , 44 , 7437 – 7439 .
   Web of Science ®Google Scholar
• Chandrasekhar , S. ; Gopalaiah , K. Beckmann reaction of oximes catalysed by chloral: Mild and neutral procedures . Tetrahedron Lett. 2003 , 44 , 755 – 756 .
   Web of Science ®Google Scholar
• Khodaei , M. M. ; Meybodi , F. A. ; Rezai , N. ; Salehi , P. Solvent-free Beckmann rearrangement of ketoximes by anhydrous ferric chloride . Synth. Commun. 2001 , 31 , 2047 – 2050 .
   Web of Science ®Google Scholar
• 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 – 6286 .
   PubMed Web of Science ®Google Scholar
• Ikushima , Y. ; Hatakeda , K. ; Sato , M. ; Stao , 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 – 2209 .
   PubMed Web of Science ®Google Scholar
• Ikushima , Y. ; Hatakeda , K. ; Stao , O. ; Yokoyama , T. ; Arai , M. Noncatalytic organic synthesis using supercritical water: The peculiarity near the critical point . Angew. Chem. Int. Ed. 1999 , 38 , 2910 – 2914 .
   PubMed Web of Science ®Google Scholar
• Ikushima , Y. ; Stao , O. ; Sato , M. ; Hatakeda , K. ; Arai , M. Innovations in chemical reaction processes using supercritical water: An environmental application to the production of ϵ-caprolactam . Chem. Eng. Sci. 2003 , 58 , 935 – 941 .
   Web of Science ®Google Scholar
• Futuya , Y. ; Ishihara , K. ; Yamamoto , H. Cyanuric chloride as a mild and active Beckmann rearrangement catalyst . J. Am. Chem. Soc. 2005 , 127 , 11240 – 11241 .
   PubMed Web of Science ®Google Scholar
• Wang , B. ; Gu , Y. ; Luo , C. ; Yang , T. ; Yang , L. ; Suo , J. Sulfamic acid as a cost-effective and recyclable catalyst for liquid Beckmann rearrangement, a green process to produce amides from ketoximes without waste . Tetrahedron Lett. 2004 , 45 , 3369 – 3372 .
   Web of Science ®Google Scholar
• Li , D. ; Shi , F. ; Guo , S. ; Deng , Y. Highly efficient Beckmann rearrangement and dehydration of oximes. Tetrahedron Lett. 2005, 46, 671–674.
   Web of Science ®Google Scholar
• Zhu , M. ; Cha , C. ; Deng , W. ; Shi , X. A mild and efficient catalyst for the Beckmann rearrangement, BOP-Cl . Tetrahedron Lett. 2006 , 47 , 4861 – 4863 .
   Web of Science ®Google Scholar
• Sardarian , A. R. ; Shahsavari-Fard , Z. ; Shahsavari , H. R. ; Ebrahini , Z. A concise synthesis of 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) and homo DMDP from L-xylose . Tetrahedron Lett. 2007 , 48 , 2369 – 2372 .
   Web of Science ®Google Scholar
• Ramalingan , C. ; Park , Y. T. Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile . J. Org. Chem. 2007 , 72 , 4536 – 4538 .
   PubMed Web of Science ®Google Scholar
• Su , W. K. ; Zhang , Y. ; Li , J. J. ; Li , P. A simple and efficient procedure for the Beckmann rearrangement of oxime using bis-(trichloromethyl) carbonate/DMF . Org. Prep. Proc. Int. 2008 , 40 , 543 – 550 .
   Web of Science ®Google Scholar
• 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 – 7793 .
   Web of Science ®Google Scholar
• 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 – 30 .
   Web of Science ®Google Scholar
• Ramalingan , C. ; Park , Y. T. An efficient and versatile one-pot Beckmann rearrangement of ketoximes using mesitylenesulfonyl chloride . Synthesis 2008 , 9 , 1351 – 1358 .
   Google Scholar
• Yadav , L. D. S. ; Srivastava , V. P. Bromodimethylsulfonium bromide (BDMS) in ionic liquid: A mild and efficient catalyst for Beckmann rearrangement . Tetrahedron Lett. 2010 , 51 , 739 – 743 .
   Web of Science ®Google Scholar
• Ganguly , N. C. ; Mondal , P. Efficient iodine-mediated Beckmann rearrangement of ketoximes to amides under mild neutral conditions . Synthesis 2011 , 8 .
   Web of Science ®Google Scholar
• 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-chlorosuccinimide . Synth. Commun. 2002 , 32 , 2535 – 2541 .
   Web of Science ®Google Scholar
• Tian , Y. P. ; Xu , F. ; Wang , Y. ; Wang , J. J. ; Li , H. L. PPh3-catalysed one-pot three-componment syntheses of α -aminophosphonates under solvent-free conditions . J. Chem. Res. 2009 , 2 , 78 – 80 .
   Web of Science ®Google Scholar
• Sato , A. ; Yorimitsu , H. ; Oshima , K. Radical phosphination of organic halides and alkyl imidazole-1-carbothioates . J. Am. Chem. Soc. 2006 , 128 , 4240 – 4241 .
   PubMed Web of Science ®Google Scholar
• Alizadeh , A. ; Sheikhi , E. One-pot synthesis of functionalized hydantoin derivatives via a four-component reaction between an amine, an arylsulfonyl isocyanate, and an alkyl propiolate or dialkyl acetylene-dicarboxylate in the presence of triphenylphosphine . Tetrahedron Lett. 2007 , 48 , 4887 – 4890 .
   Web of Science ®Google Scholar
• Yang , Y. ; Shi , M. Ring-expanding reaction of cyclopropyl amides with triphenylphosphine and carbon tetrahalide . J. Org. Chem. 2005 , 70 , 8645 – 8648 .
   PubMed Web of Science ®Google Scholar
• Lipshutz , B. H. ; Chung , D. W. ; Rich , B. ; Corral , R. Simplification of the Mitsunobu reaction: Di-p-chlorobenzyl azodicarboxylate: A new azodicarboxylate . Org. Lett. 2006 , 8 , 5069 – 5072 .
   PubMed Web of Science ®Google Scholar
• Anilkumar , G. ; Nambu , H. ; Kota , Y. A simple and efficient iodination of alcohols on polymer-supported triphenylphosphine . Org. Proc. Res. Dev. 2002 , 6 , 190 – 191 .
   Web of Science ®Google Scholar
• Ponzo , V. L. ; Bianchi , D. A. ; Kaufman , T. S. Carbonyl transposition of α -hydroxyamidals mediated by triphenylphosphine-iodine: A new entry to tetrahydroisoquinolin-4-ones . Tetrahedron Lett. 1998 , 39 , 3409 – 3412 .
   Web of Science ®Google Scholar
• Deng , W. P. ; Du , W. T. ; Pi , H. J. ; Dong , J. D. ; An , N. Unexpected results from the re-investigation of the Beckmann rearrangement of ketoximes into amides by using TsCl . Tetrahedron 2009 , 65 , 7790 – 7793 .
   Web of Science ®Google Scholar
• Hashimoto , M. ; Obora , Y. ; Sakaguchi , S. ; Ishii , Y. Beckmann rearrangement of ketoximes to lactams by triphosphazene catalyst. J. Org. Chem. 2008, 73, 2894–2897.
   PubMed Web of Science ®Google Scholar
• Sonawana , H. R. ; Lanjundiah , B. S. ; Kulkarni , D. G. ; Ahuja , J. R. A unique 1,2-shift selectivity in 2-hydroxypropiophenone dimethylacetals: Generation of new methodologies for methyl-2-arylpropanoates and 1,2-carbonyl transposition . Tetrahedron 1988 , 44 , 7319 – 7324 .
   Web of Science ®Google Scholar
• Barrillier , D. ; Levillain , J. ; Vazeux , M. Halides-based electrophiles–mediated epoxide ring-opening reactions of α,β-epoxysulfoxides in C6-series: Deoxygenation versus dehydration and an overall 1,2-keto transposition . Tetrahedron 1994 , 50 , 5413 – 5424 .
   Web of Science ®Google Scholar
• BoJitt , V. ; Mioskowski , C. ; Lee , S. G. ; Falck , J. R. Direct preparation of 2-deoxy-D-glucopyranosides from glucals without Ferrier rearrangement . J. Org. Chem. 1990 , 55 , 5812 – 5813 .
   Web of Science ®Google Scholar