BISMUTH NITRATE-MEDIATED DEPROTECTION OF OXIMES

REFERENCES

• Donaruma , L.G. and Heldt , W.Z. 1960 . The Beckmann Rearrangement . Organic Reactions , 11 : 1
   Web of Science ®Google Scholar
• Bosch , A.I. , Cruz , P. , Diez-Barra , E. , Loupy , A. and Langa , F. 1995 . Microwave Assisted Beckman Rearrangement of Ketoximes in Dry Media . Synlett , : 1259 and references cited therein
   Google Scholar
• Maloney , J.R. , Lyle , R.E. , Scavedra , J.E. and Lyle , G.G. 1978 . Oxidative Deoximation with Pyridinium Chlorochromate . Synthesis , : 212
   Web of Science ®Google Scholar
• Drabowicz , J. 1980 . Rapid Deoximation with Pyridinium Chlorochromate/Hydrogen Peroxide System . Synthesis , : 125
   Web of Science ®Google Scholar
• Shim , S. , Kim , K. and Kim , Y.H. 1987 . Direct Conversion of Oximes and Hydrazones into Their Ketones with Dinitrogen Tetroxide . Tetrahedron Lett. , 28 : 645
   Web of Science ®Google Scholar
• Aizpurua , J.M. , Juaristi , M. , Lecea , B. and Palomo , C. 1985 . Reagents and Synthetic methods—40 Halosilanes/Chromium Trioxide as Efficient Oxidizing Reagents . Tetrahedron , 41 : 2903
   Web of Science ®Google Scholar
• Ranu , B.C. and Sarkar , D.C. 1988 . A Simple, Efficient, and Highly Selective Method for the Regeneration of Carbonyl Compounds from Oximes and Semicarbazones . J. Org. Chem. , 53 : 878
   Web of Science ®Google Scholar
• Olah , G.A. , Liao , Q. , Lee , C.S. and Surya Prakash , G.K. 1993 . Considered as Synthetic Methods and Reactions. 183. Efficient and mild Oxidation of Ketoximes to Their Parent Ketones with Dimethyldioxirane . Synlett , : 427
   Google Scholar
• Curini , M. , Rosati , O. and Pisani , E. 1996 . Heterogeneous Catalysis in Carbonyl Regeneration from Oximes, Semicarbazones, and Tosylhydrazones by Zirconium Sulfophenyl Phosphonate . Synlett , : 333
   Google Scholar
• Varma , R.S. and Meshram , H.M. 1997 . Solid State Cleavage of Semicarbazones and Phenylhydrazones with Ammonium Persulfate-clay Using Microwave or Ultrasonic Irradiation . Tetrahedron Lett. , 38 : 7973
   Web of Science ®Google Scholar
• Varma , R.S. , Dahiya , R. and Saini , R.K. 1997 . Solid State Regeneration of Ketones from Oximes on Wet Silica Supported Sodium Periodate Using Microwaves . Tetrahedron Lett. , 38 : 8819
   Web of Science ®Google Scholar
• Becker , F.F. and Banik , B.K. 1998 . Polycyclic Aromatic Compounds as Anticancer Agents: Synthesis & Biological Evaluation of Some Chrysene Derivatives . Bioorg. & Med. Chem. Lett. , 8 : 2877
   PubMed Web of Science ®Google Scholar
• Banik , B.K. and Becker , F.F. 2001 . Synthesis, Electrophilic Substitution and Structure–Activity Relationship Studies of Polycyclic Aromatic Compounds for the Development of Anticancer Agents . Curr. Med. Chem. , : 000
   Google Scholar
• Banik , B.K. and Becker , F.F. 2001 . Polycyclic Aromatic Compounds as Anticancer Agents: 4. Structure–Activity Relationships of Chrysene and Pyrene Derivatives . Bioorg. & Med. Chem. , 9 : 593
   PubMed Web of Science ®Google Scholar
• Becker , F.F. , Mukhopadhyay , C. , Hackfeld , L. , Banik , I. and Banik , B.K. 2000 . Polycyclic Aromatic Compounds as Anticancer Agents: Synthesis and Biological Evaluation of Dibenzofluorene Derivatives . Bioorg. & Med. Chem. , 8 : 2693
   PubMed Web of Science ®Google Scholar
• Samajdar , S. , Becker , F.F. and Banik , B.K. 2000 . Surface-mediated Highly Efficient Regioselective Nitration of Aromatic Compounds by Bismuth Nitrate . Tetrahedron Lett. , 41 : 8017
   Web of Science ®Google Scholar
• A representative procedure is as follows: To a suspension of oximes (1 mmol) in silica gel (1.5 g) and THF (10 mL) was added bismuth nitrate pentahydrate (485 mg, 1 mmol) and water (2 mL). The mixture was refluxed for the specified time as indicated in the Table 1. It was then filtered to remove the silica gel, extracted with dichloromethane (25 mL), washed successively with saturated sodium bicarbonate solution, dried, evaporated and filtered through a short silica gel column to obtain the pure ketone
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