Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 13
149
Views
19
CrossRef citations to date
0
Altmetric
Original Articles

Product Selectivity in Semiconductor-Mediated Dehydrazonation of Benzophenone Hydrazone

, &
Pages 1929-1937 | Received 06 Dec 2009, Published online: 02 May 2011

REFERENCES

  • Greene , T. W. ; Wuts , P. G. Protective Groups in Organic Synthesis, , 3rd ed. ; Wiley : New York , 1999 ; pp. 47 – 53 .
  • Barton , D. H. R. ; Beaton , J. M. A synthesis of aldosterone acetate . J. Am. Chem. Soc. 1961 , 83 , 4083 – 4089 .
  • Hosseinzadeh , R. ; Tajbakshsh , M. ; Niaki , M. Y. 2,6-Dicarboxypyridinium chlorochromate: A mild, efficient, and selective reagent for oxidative deprotection of oximes to carbonyl compounds . Tetrahedron Lett. 2002 , 43 , 9413 – 9415 .
  • Salehi , P. ; Khodaei , M. M. ; Goodarzi , M. A mild and selective deoximation method using γ-picolinium chlorochromate (γ-pcc) . Synth. Commun. 2002 , 32 , 1253 – 1263 .
  • Khazaei , A. ; Vaghei , R. G. Facile regeneration of carbonyl compounds from oximes using poly[4-vinyl-N,N-dichlorobenzenesulfonamide] . Tetrahedron Lett. 2002 , 43 , 3073 – 3074 .
  • Barton , D. H. R. ; Lester , D. J. ; Ley , S. V. Oxidation of ketone and aldehyde hydrazones, oximes, and semicarbazones and of hydroxylamines and hydrazo-compounds using benzeneseleninic anhydride . J. Chem. Soc. Perkin Trans. 1 1980 , 11 , 1212 – 1217 .
  • Shim , S. B. ; Kim , K. ; Kim , Y. H. Direct conversion of oximes and hydrazones into their ketones with dinitrogen tetroxide . Tetrahedron Lett. 1987 , 28 , 645 – 648 .
  • Bose , D. S. ; Narraiah , A. V. A facile method for the conversion of oximes and tosylhydrazones to carbonyl compounds with Dess–Martin periodinane . Synth. Commun. 1999 , 29 , 937 – 941 .
  • Nattier , B. A. ; Eash , K. J. ; Mohan , R. S. Deprotection of ketoximes using bismuth(III) nitrate pentahydrate. Synthesis 2001, 1010–1012.
  • Bandgar , B. P. ; Shaikh , S. I. ; Iyer , S. Oxidative deoximation with sodium perborate . Synth. Commun. 1996 , 26 , 1163 – 1168 .
  • Olah , G. A. ; Aravanaghi , M. ; Parakash , G. K. S. Synthetic methods and reactions: Reductive cleavage of oximes with vanadium(II) chloride . Synthesis 1980 , 79 , 220 – 221 .
  • Hill , C. L. Introduction: Polyoxometalates multicomponent molecular vehicle to probe fundamental issues and practical problems . Chem. Res. 1998 , 98 , 1 – 2 .
  • Keggin , J. F. Structure of the molecule of i2-phosphotungstic . Nature 1933 , 131 , 908 – 909 .
  • Misono , M. Heterogeneous catalysis by heteropoly compounds of molybdenum and tungsten . Catal. Rev. Sci. Eng. 1987 , 29 , 269 – 321 .
  • Kozhevnikov , I. V. Heteropoly acids and related compounds as catalysts for fine chemical synthesis . Catal. Rev. Sci. Eng. 1995 , 37 , 311 – 352 .
  • Hersberg , E. B. Regeneration of steroid ketones from their semicarbazones with pyruvic acid . J. Org. Chem. 1948 , 13 , 542 – 546 .
  • Shiraishi , Y. ; Hirai , T. Selective organic transformations on titanium oxide–based photocatalysts . J. Photochem. Photobiol. C 2008 , 9 , 157 – 170 .
  • Selvam , K. ; Swaminathan , M. A green chemical synthesis of 2-alkylbenzimidazoles from 1,2-phenylenediamine and propylene glycol or alcohols mediated by Ag-TiO2/clay composite photocatalyst . Chem. Lett. 2007 , 36 , 1060 – 1061 .
  • Pal , B. ; Torimoto , T. ; Okazaki , K. ; Ohtani , B. Photocatalytic syntheses of azoxybenzene by visible light irradiation of silica-coated cadmium sulfide nanocomposites . Chem. Commun. 2007 , 5 , 483 – 485 .
  • Pal , B. ; Ikeda , S. ; Kominami , H. ; Kera , Y. ; Ohtani , B. Photocatalytic redox-combined synthesis of L-pipecolinic acid from L-lysine by suspended titania particles: Effect of noble metal loading on the selectivity and optical purity of the product . J. Catal. 2003 , 217 , 152 – 159 .
  • Tada , H. ; Kubo , M. ; Inubushi , Y. ; Ito , S. N=N bond cleavage of azobenzene through Pt/TiO2 photocatalytic reduction . Chem. Commun. 2000 , 11 , 977 – 978 .
  • Muthu , K. ; Selvam , K. ; Krishnakumar , B. ; Swaminathan , M. Energy-efficient regeneration of ketones from oximes using semiconductor photocatalysts . Appl. Catal. A 2009 , 358 , 259 – 263 .
  • Zhang , F. ; Guan , N. ; Li , Y. ; Zhang , X. ; Chen , J. ; Zeng , H. Control of morphology of silver clusters coated on titanium dioxide during photocatalysis . Langmuir 2003 , 19 , 8230 – 8234 .
  • Sa , J. ; Garcia , M. F. ; Anderson , J. A. Photoformed electron transfer from TiO2 to metal clusters . Catal. Commun. 2008 , 9 , 1991 – 1995 .
  • Vogel , A. I. A Textbook of Practical Organic Chemistry, , 3rd ed. ; ELBS Longman : London , 1975 ; pp. 491 – 512 .
  • Sobana , N. ; Muruganandham , M. ; Swaminathan , M. Nano-Ag particles doped TiO2 for efficient photodegradation of direct azo dyes . J. Mol. Catal. A 2006 , 258 , 124 – 132 .

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.