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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 16
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Original Articles

Mild, Efficient, and Greener Dethioacetalization Protocol Using 30% Hydrogen Peroxide in Catalytic Combination with Ammonium Iodide

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Pages 2374-2384 | Received 12 Mar 2010, Published online: 14 Jun 2011

REFERENCES

  • Greene , T. W. ; Wuts , P. G. M. Protective Groups in Organic Synthesis, , 3rd ed. ; John Wiley and Sons : New York , 1999 ; pp. 333 – 344 .
  • Seebach , D. Methods of reactivity umpolung . Angew Chem., Int. Ed. Engl. 1979 , 18 , 239 – 258 .
  • Burghardt , T. E. Developments in the deprotection of thioacetals . Sulfur Chem. 2005 , 26 , 411 – 427 .
  • Nishide , K. ; Yokota , K. ; Nakamura , D. ; Sumiya , T. ; Node , M. ; Ueda , M. ; Fuji , K. A new entry for the deprotection of monothioacetals and dithioacetals: Silver nitrite-iodine system . Tetrahedron Lett. 1993 , 34 , 3425 – 3428 .
  • Corey , E. J. ; Ericson , B. W. Oxidative hydrolysis of 1, 3-dithiane derivatives to carbonyl compounds using N-halosuccinimide reagents . J. Org. Chem. 1971 , 36 , 3553 – 3560 .
  • (a) Jones , P. S. ; Ley , S. V. ; Simkins , N. S. ; Whittle , A. J. Total synthesis of the insect antifeedant a jugarin I and degradation studies of related clerodane diterpene. Tetrahedron 1986, 42, 6519–6534; (b) Haroutounian , S. A. Selenium(IV) oxide mediated cleavage of 1,3-dithiolanes: A convenient method of dedithioacetalization. Synthesis 1995, 39–40.
  • Fetizon , M. ; Jurion , M. Aldehydes and ketones from thioacetals . J. Chem. Soc., Chem. Commun. 1972 , 382 – 383 .
  • (a) Varma , R. S. ; Saini , R. K. Solid state dethioacetalization using clayfen . Tetrahedron Lett. 1997 , 38 , 2623 – 2624 ; (b) Gupta , N. ; Sonu ; Kad , G. L. ; Singh , J. Acidic ionic liquid [bmim]HSO4: An efficient catalyst for acetalization and thioacetalization of carbonyl compounds and their subsequent deprotection . Catal. Commun. 2007 , 8 , 1323 – 1328 ; (c) Desai , M. V. ; Pore , D. M. ; Tamhankar , B. V. ; Jaghav , S. A. ; Wadgaonkar , P. P. An efficient deprotection of dithioacetals to carbonyls using Oxone-KBr in aqueous acetonitrile . Tetrahedron Lett. 2006 , 47 , 8559 – 8561 ; (d) Kamal , A. ; Reddy , P. S. M. M. ; Rajasekhar Reddy , D. An efficient catalytic deprotection of thioacetals employing bismuth triflate: Synthesis of pyrrolo[2,1-c][1,4] benzodiazepines . Tetrahedron Lett. 2003 , 44 , 2857 – 2860 ; (e) Bandgar , B. P. ; Kasture , S. P. Natural kaolinitic clay: A remarkable reusable solid catalyst for the selective cleavage of thioacetals without solvent . Green. Chem. 2000 , 154 – 156 ; (f) Barhate , N. B. ; Shinde , P. D. ; Mahajan , V. A. ; Wakharkar , R. D. A convenient oxidative demasking of 1,3-dithiolanes and dithianes to carbonyl compounds with TBHP . Tetrahedron Lett. 2002 , 43 , 6031 – 6033 ; (g) Oksdath-Mansilla , G. ; Peñéñory , A. B. Simple and efficient deprotection of 1,3- dithianes and 1,3-dithiolanes by copper(II) salts under solvent-free conditions . Tetrahedron Lett. 2007 , 48 , 6150 – 6154 .
  • Stork , G. ; Zhao , K. A simple method of dethioacetalization . Tetrahedron Lett. 1989 , 30 , 287 – 290 .
  • Langville , N. F. ; Dakin , L. A. ; Panek , J. S. A mild, chemoselective protocol for the removal of thioketals and thioacetals mediated by Dess–Martin periodinane . Org. Lett. 2003 , 5 , 575 – 578 .
  • (a) Nicolaou , K. C. ; Mathison , C. J. N. ; Montagnon , T. o-Iodoxybenzoic acid (IBX) as a viable reagent in the manipulation of nitrogen- and sulfur-containing substrates: Scope, generality, and mechanism of IBX-mediated amine oxidation and dithiane deprotections . J. Am. Chem. Soc. 2004 , 126 , 5192 – 5201 ; (b) Krishnaveni , N. S. ; Surendra , K. ; Nageshwar , Y. V. D. ; Rao , K. R. Mild and efficient hydrolysis of aromatic thioacetals/thioketals using o-iodoxybenzoic acid (IBX) in the presence of β-cyclodextrin in water . Synthesis 2003 , 2295 – 2297 .
  • Gammon , D. W. ; Kinfe , H. H. ; Devos , D. E. ; Jacobs , P. A. ; Sels , B. F. A simple, efficient alternative for highly stereoselective iodohydroxylation of protected glycals . Tetrahedron Lett. 2004 , 45 , 9533 – 9536 .
  • Narender , N. ; Reddy , K. S. K. ; Krishna Mohan , K. V. V. ; Kulkarni , S. J. Eco-friendly oxyiodination of aromatic compounds using ammonium iodide and hydrogen peroxide . Tetrahedron Lett. 2007 , 48 , 6124 – 6128 .
  • (a) Ganguly , N. C. ; Datta , M. Mild and eco-friendly oxidative cleavage of 1,3- dithianes and 1,3-dithiolanes with a catalytic amount of hydrobromic acid and hydrogen peroxide: Synergetic effect of bromonium ion equivalent and hydrogen peroxide. J. Chem. Res., Synop. 2005, 218–221; (b) Ganguly , N. C. ; Datta , M. Eco-friendly solid-state oxidative deprotection of 1,3-dithianes and 1,3-dithiolanes using ammonium persulfate on wet montmorillonite K-10 clay support under microwave irradiation. Synlett 2004, 659–662; (c) Ganguly , N. C. ; Barik , S. K. A facile, catalytic deoximation method using potassium bromide and ammonium heptamolybdate in the presence of hydrogen peroxide in an aqueous medium. Synthesis 2008, 425–428; (d) Ganguly , N. C. ; Barik , S. K. A facile mild deprotection protocol for 1,3-dithianes and 1,3-dithiolanes with 30% hydrogen peroxide and iodine catalyst in aqueous micellar system. Synthesis 2009, 1393–1399; (e) Ganguly , N. C. ; Nayek , S. ; Barik , S. K. A convenient mild catalytic deprotection of oximes to carbonyl compounds with hydrogen peroxide and iodine catalyst in aqueous acetonitrile. Synth. Commun. 2009, 39, 4053–4061.
  • Cerritelli , S. ; Chiarini , M. ; Cerichelli , G. ; Capone , M. ; Marsili , M. Supramolecular assemblies as promoters of iodohydrin formation . Eur. J. Org. Chem. 2004 , 623 – 630 .
  • 1,3-Dithianes, 1,3-dithiolanes, and other thioacetals/ketals were prepared following literature procedures : (a) Hatch , R. P. ; Shringarpure , J. ; Weinreb , S. M. Studies on total synthesis of the olivomycins . J. Org. Chem. 1978 , 43 , 4172 – 4177 ; (b) Marshall , J. A. ; Belletire , J. L. Heterolytic fragmentation of 1,3-dithianyl tosylates . Tetrahedron Lett. 1971 , 12 , 871 – 874 .
  • (a) LeBlond , C. R. ; Rossen , K. ; Gortsema , F. P. ; Zavialov , I. A. ; Cianciosi , S. J. ; Andrews , A. T. ; Sun , Y. Harvesting short-lived hypoiodous acid for efficient diastereoselective iodohydroxylation in Crixivan R synthesis . Tetrahedron Lett. 2001 , 42 , 8603 – 8606 ; (b) Lengyel , I. ; Epstein , I. R. ; Kustin , K. Kinetics of iodine hydrolysis . Inorg. Chem. 1993 , 32 , 5880 – 5882 ; (c) Cotton , F. A. ; Wilkinson , G. Advanced Inorganic Chemistry, 5th ed.; John Wiley & Sons, 1988 .
  • (a) Vogel , A. I. A Textbook of Practical Organic Chemistry, , 3rd ed. ; ELBS and Longman Group Ltd. : London , 1973 ; (b) Miranda , R. ; Osnaya , R. ; Garduñ , R. ; Delgado , F. ; Álvarez , C. ; Salmon , M. A general alternative to obtain S,S-acetals using taff, a bentonitic clay, as the catalyst. Synth. Commun. 2001, 31, 1587-1597; (c) Khan , A. T. ; Mondal , E. ; Ghosh , S. ; Islam , S. A simple and practical synthetic protocol for acetalisation, thioacetalisation, and transthioacetalisation of carbonyl compounds under solvent-free conditions. Eur. J. Org. Chem. 2004, 9, 2002–2009 .

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