Regeneration of Aromatic Carbonyl Compounds from the Corresponding Oximes Using Tetrapyridine Silver(II) Peroxydisulfate in Acetonitrile and Aqueous Media

REFERENCES

• Greene , J. G. ; Wuts , P. G. M. Protective Goups in Organic Synthesis, , 2nd ed. ; John Wiley & Sons : New York , 1991 ; pp. 175 .
   Google Scholar
• Cheronis , N. D. ; Entrikin , J. B. Identification of Organic Compounds ; Interscience : New York , 1963 .
   Google Scholar
• Massey , E. H. ; Kitchell , B. ; Martin , L. D. ; Gerzon , K. ; Murphy , H. W. Erythromycylamine. Tetrahedron Lett. 1970, 157.
   PubMedGoogle Scholar
• Stevens , R. V. ; Gaeta , F. C. A. ; Lawrence , D. Camphorae: chiral intermediates for the enantiospecific total synthesis of steroids . J. Am. Chem. Soc. 1983 , 105 , 7713 .
   Web of Science ®Google Scholar
• Corsaro , A. ; Chiacchio , U. ; Pistara , V. Regeneration of carbonyl compounds from the corresponding oximes . Synthesis 2001 , 13 , 1903 .
   Google Scholar
• (a) Perkin , W. H. ; Roberts , W. M. ; Robison , R. 2-Diketohydrindene . J. Chem. Soc. 1912 , 101 , 232 ; (b) Rottig , W. Über eine einfache Synthese des antiken Purpurs . J. Prakt. Chem. 1935 , 142 , 35 ; (c) Deck , L. M. ; Jagt , D. L. V. ; Royer , R. E. Gossypol and derivatives: A new class of aldose reductase inhibitors . J. Med. Chem. 1991 , 34 , 3301 ; (d) Abazid , M. ; Bertrand , H. O. ; Christen , M. O. ; Burgot , J. L. A general synthesis of new dithiolethione derivatives: 5-(1-Hydroxyimino alkyl)-1,2-dithiole-3-thiones and 5-acyl-i,2-dithiole-3-thiones . Phosphorus, Sulfur Silicon Relat. Elem. 1994 , 1 , 195 .
   Google Scholar
• Müller , E. ; Böttcher , E. Photooximierung von methylgruppen in gesättigten aliphatischen kohlenwasserstoffen . Tetrahedron Lett. 1970 , 35 , 3086 .
   Google Scholar
• (a) Firouzabadi , H. ; Seddighi , M. ; Arab Ahmadi , Z. ; Sardarian , A. R. Selective oxidative cleavage of benzylic carbon-nitrogen double bonds under non-aqueous condition with tetrakis(pyridine)-silver dichromate [(Py)2Ag]2 Cr2O7 . Synth. Commun. 1989 , 19 , 3385 ; (b) Tamami , B. ; Goudarizian , N. Poly(vinylpyridine N-oxide)–supported dichromates as new effective, mild, and versatile oxidizing reagents for various organic compounds . Eur. Polym. J. 1992 , 28 , 1035 ; (c) Baltork , I. M. ; Pouranshirvani , S. 3-Carboxypyridinium chlorochromate: An inexpensive and efficient reagent for cleavage of carbon-nitrogen double bonds under non-aqueous condition . Synth. Commun. 1996 , 26 , 1 ; (d) Firouzabadi , H. ; Iranpoor , N. ; Kiaeezadeh , F. ; Toofan , J. Chromium(VI) based oxidants-1: Chromium peroxide complexes as versatile, mild, and efficient oxidants in organic synthesis . Tetrahedron 1986 , 42 , 719 ; (e) Firouzabadi , H. ; Iranpoor , N. ; Parham , H. ; Tootan , J. Bis[trinitratocerium(IV)]chromate [Ce(N03)312Cr04; A mild oxidant in organic synthesis . Synth. Commun. 1984 , 14 , 631 .
   Web of Science ®Google Scholar
• (a) Wali , A. ; Ganeshpure , P. A. ; Satish , S. Potassium permanganate oxidation of ketone oximes: A deprotective version . Bull. Chem. Soc. Jpn. 1993 , 66 , 1847 ; (b) Jadhav , V. K. ; Wadgaonkar , P. P. ; Joshi , P. L. ; Salunkhe , M. M. Oxidation of oximes to ketones with zeolite supported permanganate . Synth. Commun. 1999 , 29 , 1989 ; (c) Firouzabadi , H. ; Mottaghineiad , E. ; Seddighi , M. Barium permangante: A useful oxidant for the selective deoximation of benzylic oximes to their corresponding carbonyl compounds . Synth. Commun. 1989 , 19 , 3469 .
   Web of Science ®Google Scholar
• (a) McKillop , A. ; Hunt , J. D. ; Taylor , E. C. ; Kienze , F. Thallium in organic synthesis, XX: Oxidative rearrangement of olefins with thallium(III) nitrate: A simple one-step synthesis of aldehydes and ketones . Tetrahedron Lett. 1970 , 5275 ; (b) McKillop , A. ; Hunt , J. D. ; Naylor , R. D. ; Taylor , E. C. Thallium in organic synthesis, XXVI: Direct conversion of oximes into aldehydes and ketones with thallium(III) nitrate (TTN) . J. Am. Chem. Soc. 1971 , 93 , 4918 .
   Google Scholar
• Bird , J. W. ; Diaper , D. G. M. Preparative conversion of oximes to parent carbonyl compounds by cerium(IV) oxidation . Can. J. Chem. 1969 , 47 , 145 .
   Web of Science ®Google Scholar
• Yukawa , Y. ; Sakai , M. ; Suzuki , S. The reactions of oximes with lead tetraacetate: The scope of the reactions . Bull. Chem. Soc. Jpn. 1966 , 39 , 2266 .
   Google Scholar
• (a) Olah , G. A. ; Vankar , Y. D. ; Surya Prakash , G. K. Synthetic methods and reactions: Oxidative cleavage of ketoximes and tosylhydrazones with aqueous bromine . Synthesis 1979 , 113 ; (b) Yadav , J. S. ; Sasmal , P. K. ; Chand , P. K. Iodine as a new deoximating agent . Synth. Commun. 1999 , 29 , 3667 .
   Google Scholar
• (a) Bandgar , B. P. ; Kale , R. R. ; Kunde , L. B. Selective regeneration of carbonyl compounds from oximes with N-bromosuccinimide under neutral and mild conditions. Monatsh. Chem. 1998, 129, 1057; (b) Bandgar , B. P. ; Kunde , L. B. ; Thote , J. C. Deoximation with N-haloamides. Synth. Commun. 1997, 27, 1149; (c) Fu , X. ; Cook , J. M. General approach for the synthesis of ajmaline-related alkaloids: Enantiospecific total synthesis of (−)-suaveoline, (−)-raumacline, and (−)-Nb-methylraumacline. J. Org. Chem. 1993, 58, 661.
   Google Scholar
• Olah , G. A. ; Welch , J. ; Parakash , G. K. S. ; Ho , T. L. Synthetic methods and reactions, XXIV: Oxidative cleavage of hydrazones with molybdenyl chloride (MoOCl3) or molybdenum hexafluoride and reductive cleavage of oximes with molybdenyl chloride/zinc . Synthesis 1976 , 808 .
   Google Scholar
• Pojer , P. M. The use of sodium dithionite for the reduction of imines and the cleavage of oximes . Aust. J. Chem. 1979 , 32 , 201 .
   Web of Science ®Google Scholar
• Nitta , M. ; Sasaki , I. ; Miyano , M. ; Kobayashi , Y. Deoximation of oxime O-acetates, oximes, and oxime ethers by nonacarbonyldiiron or pentacarbonyliron: An electronic effect for the N–O bond cleavage . Bull. Chem. Soc. Jpn. 1984 , 57 , 3357 .
   Google Scholar
• Balicki , R. ; Kaczmarek , L. Mild reductive deoximation with TiCl4/NaI reagent system . Synth. Commun. 1991 , 21 , 1777 .
   Web of Science ®Google Scholar
• (a) Vakatar , V. V. ; Tatake , J. G. ; Sunthankar , S. V. A mild and efficient method for the reduction of oximes to imines for futher in situ reactions . Chem. Ind. (London) 1977 , 742 ; (b) Olah , G. A. ; Arvanaghi , M. ; Prakash , G. K. S. Synthetic methods and reactions 79: Reductive cleavage of oximes with vanadium(II) chloride . Synthesis 1980 , 220 .
   Google Scholar
• Kamal , A. ; Rao , M. V. ; Meshram , H. M. Enzymatic deoximation of oximes by ultrasonically stimulated baker's yeast . J. Chem. Soc., Perkin Trans. 1 1991 , 2056 .
   Google Scholar
• (a) Varma , R. S. ; Dahiya , R. ; Saini , R. K. Iodobenzene diacetate on alumina: Rapid oxidation of alcohols to carbonyl compounds in solventless system using microwaves . Tetrahedron Lett. 1997 , 38 , 7029 ; (b) Oussaid , A. ; Thach , I. N. ; Loupy , A. Selective dealkylations of alkyl aryl ethers in heterogeneous basic media under microwave irradiation . Tetrahedron Lett 1997 , 38 , 2451 .
   Web of Science ®Google Scholar
• House , D. A. Kinetics and mechanism of oxidations by peroxydisulfate . Chem. Rev. 1962 , 62 , 185 .
   Web of Science ®Google Scholar
• Chen , F. ; Liu , A. ; Yan , Q. ; Liu , M. ; Zhang , D. ; Shao , L. Tetrabutylammonium peroxydisulfate in organic synthesis: An efficient, highly selective and oxidative deoximation by tetrabutylammonium peroxydisulfate . Synth.Commun. 1999 , 29 , 1049 .
   Web of Science ®Google Scholar
• Hajipour , A. R. ; Mohammadpoor-Baltork , I. ; Kianfar , G. Bis(1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane) peroxodisulfate: A mild and efficient oxidant for cleavage of nitrogen double bonds and oxidation of alcohols under anhydrous conditions . Bull. Chem. Soc. Jpn. 1998 , 71 , 2655 .
   Web of Science ®Google Scholar
• (a) Mohammadpoor-Baltork , I. ; Sadeghi , M. M. ; Mahmoodi , N. ; Kharamesh , B. n-Butyltriphenylphosphonium dichromate: An efficient and selective oxidizing agent . Indian J. Chem., Sect. B 1997 , 36 , 438 ; (b) Mohammadpoor-Baltork , I. ; Hajipour , A. R. ; Mohammadi , N. Benzyltriphenylphosphonium peroxodisulfate (PhCH2PPh3)2S2O8: A mild and inexpensive reagent for efficient oxidation of organic compounds under nonaqueous and aprotic conditions . Bull. Chem. Soc. Jpn. 1998 , 71 , 1649 .
   Google Scholar
• Minghu , W. ; Guichun , Y. ; Zuxing , C. Polymer-supported peroxodisulfate: A mild and clean oxidation of organic compounds under nonaqueous and aprotic conditions . React. Funct. Polym. 2000 , 44 , 97 .
   Web of Science ®Google Scholar
• Lakouraj , M. M. ; Bahrami , K. Amberlyst A-26–suppported peroxodisulfate, part 1: An efficient reagent for selective carbon–nitrogen double bond cleavage of oximes . J. Chem. Res., Synop. 2000 , 222 .
   Google Scholar
• Mohammadpoor-Baltork , I. ; Hajipour , A. R. ; Haddadi , R. n-Butyltriphenylphosphonium peroxodisulfate (n-BuPPh3)2S2O8: An efficient and inexpensive reagent for the cleavage of carbon–nitrogen double bonds under non-aqueous and aprotic conditions. J. Chem. Res. Synop. 1999, 102.
   Google Scholar
• (a) Angelici , R. J. Synthesis and Technique in Inorganic Chemistry, , 2nd ed. ; Saunders Company : London , 1977 ; p. 185 ; (b) Firouzabadi , H. ; Salehi , P. ; Seddighi , M. ; Sardarian , A. R. Oxidation of benzylic hydrocarbons to carbonyl compounds by tetrapyridinesilver(II) peroxydisulfate Ag(Py)4S2O8 under non-aqueous and aprotic condition. Synth. Commun. 1991, 21, 1121 ; (c) Firouzabadi , H. ; Salehi , P. ; Mohammadpoor-Baltork , I. Tetrakis(pyridine)silver(II) peroxodisulfate, [Ag(py)4]S2O8, a reagent for the oxidative transformations. Bull. Chem. Soc. Jpn. 1992, 65, 2878 .
   Google Scholar