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Solvent-Free Oxidation of Benzoins using Oxone on Wet Alumina under Microwave Irradiation

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Molecules Online

Abstract

In a solvent-free system, Oxone on wet alumina oxidizes a variety of benzoins under the influence of microwaves. This rapid method circumvents the solubility limitations of Oxone in organic solvents and its use in solvents that may not be compatible at elevated temperatures.

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References

  1. Fieser LF, Fieser M (1967) In: Reagents for organic synthesis, vol 1. Wiley, New York, p 952

    Google Scholar 

  2. (a) Trost BM, Curren DP (1981) Tetrahedron Lett 22:1287; (b) Davis FA, Lal SG, Durst HD (1988) J Org Chem 53:5004

    Article  CAS  Google Scholar 

  3. (a) Curci R, Fiorentino M, Troisi L, Edwards JO, Pater RH (1980) J Org Chem 45:4758; (b) Bloch R, Abecassis J, Hassan D (1985) J Org Chem 50:1544; (c) Denmark SE., Wu Z (1997) J Org Chem 62:8964

    Article  CAS  Google Scholar 

  4. Cicala G, Curci R, Fiorentino M, Laricchiuta O (1982) J Org Chem 47:2670

    Article  CAS  Google Scholar 

  5. Corey PF, Ward FE (1986) J Org Chem 51:1925

    Article  CAS  Google Scholar 

  6. (a) Davis FA, Chattopadhyay S, Towson JC, Lal S, Reddy T (1988) J Org Chem 53:2087; (b) Brik ME (1995) Tetrahedron Lett 36:5519; (c) Web K, Seneviratne V (1993) Tetrahedron Lett 36:2377; (d) Web K, Levy D (1995) Tetrahedron Lett 36:5117; (e) Ceccherelli P, Curini M, Epifano F, Marcotullio MC, Rosati O (1995) J Org Chem 60:8412; (f) Zhu W, Ford WT (1991) J Org Chem 56:7022; (g) Hirano M, Oose M, Morimoto T (1991) Bull Chem Soc Jpn 64:1046

    Article  CAS  Google Scholar 

  7. For cleavage-deprotection reactions see: (a) Varma RS, Chatterjee AK, Varma M (1993) Tetrahedron Lett 34:3207; (b) Varma RS, Chatterjee AK, Varma M (1993) Tetrahedron Lett 34:4603; (c) Varma RS, Varma M, Chatterjee AK (1993) J Chem Soc, Perkin Trans 1:999; (d) Varma RS, Lamture JB, Varma M (1993) Tetrahedron Lett 34:3029; (e) Varma RS, Saini RK (1997) Tetrahedron Lett 38:2623; (f) Varma RS, Meshram HM (1997) Tetrahedron Lett 38:5427; (g) Varma RS, Meshram HM (1997) Tetrahedron Lett 38:7973; (h) Varma RS, Dahiya R, Saini RK (1997) Tetrahedron Lett 38:8819. For condensation-cyclization reactions see: (i) Varma RS, Dahiya R, Kumar S (1997) Tetrahedron Lett 38:2039; (j) Varma RS, Dahiya R (1997) Synlett 1245; (k) Varma RS, Dahiya R, Kumar S (1997) Tetrahedron Lett 38:5131; (l) Varma RS, Saini RK (1997) Synlett 857. For oxidation reactions see: (m) Varma RS, Dahiya R (1997) Tetrahedron Lett 38:2043; (n) Varma RS, Saini RK, Meshram HM (1997) Tetrahedron Lett 38:6525; (o) Varma RS, Dahiya R, Saini RK (1997) Tetrahedron Lett 38:7029; (p) Varma RS, Dahiya R, Saini RK (1997) Tetrahedron Lett 38:7823; (q) Varma RS, Dahiya R (1998) Tetrahedron Lett (in press). For reduction reactions see: (r) Varma RS, Saini RK (1997) Tetrahedron Lett 38:4337

  8. Clarke HT, Dreger EE (1941) Organic Synthesis, Coll 1: 87

    Google Scholar 

  9. McKillop A, Swann BP, Ford ME, Taylor EC (1973) J Am Chem Soc 95:3641

    Article  CAS  Google Scholar 

  10. Hammond GS, Wu C-HS (1973) J Am Chem Soc 95:8215

    Article  CAS  Google Scholar 

  11. Girara P, Kagan HB (1975) Tetrahedron Lett 4513

  12. Besemann M, Cornelis A, Laszlo P (1984) C R Acad Sci Ser C 299:427

    CAS  Google Scholar 

  13. Zhang G-S, Shi Q-Z, Chen M-F, Cai K (1997) Synth Commun 27:9534

    Google Scholar 

  14. (a) McKillop A, Young DW (1979) Synthesis 401,481; (b) Laszlo P (1987) Preparative chemistry using supported reagents. Academic Press, San Diego; (c) Clark JH (1994) Catalysis of organic reactions by supported inorganic reagents. VCH, NY

  15. For recent reviews on microwave-assisted chemical reactions see (a) Abramovich RA (1991) Org Prep Proced Int 23:683; (b) Whittaker AG, Mingos DMP (1994) J Microwave Power Electromagn Energy 29:195; (c) Majetich G, Hicks R (1995) J Microwave Power Electromagn Energy 30:27; (d) Caddick S (1995) Tetrahedron 51:10,403; (e) Varma RS (1997) Microwave-assisted reactions under solvent-free ‘dry’ conditions. In: Clark DE, Sutton WH, Lewis DA (eds) Microwaves: theory and application in material processing IV. American Ceramic Society, Ceramic Transactions 80, pp 375–365

    Article  Google Scholar 

  16. (a) Gedye R, Smith F, Westaway K, Ali H, Baldisera L, Laberge L, Rousell J (1986) Tetrahedron Lett 27:279; (b) Giguere RJ, Namen AM, Lopez BO, Arepally A, Ramos DE, Majetich G, Defrauw J (1987) Tetrahedron Lett 28:6553; (c) Bose AK, Banik BK, Lavlinskaia N, Jayaraman M, Manhas MS (1997) Chemtech 27:18

    Article  CAS  Google Scholar 

  17. (a) Oussaid A, Thach LN, Loupy A (1997) Tetrahedron Lett 38:2451; (b) Villemin D, Benalloum A (1991) Synth Commun 21:1,63; (c) Lerestif JM, Toupet L, Sinbandhit S, Tonnard F, Bazureau JP, Hamelin J (1997) Tetrahedron 53:6351

    Article  CAS  Google Scholar 

  18. Aldrich Catalog Handbook of Fine Chemicals, USA, 1996–97, p 1168

  19. Raner D, Strauss C, Vyskoc RF, Mokbel L (1993) J Org Chem 58:950. The temperature of the reaction mixture inside the alumina bath (heat sink) in a Sears Kenmore microwave oven equipped with a turntable at 20% power (full power 900 Watts) reached ∼75 °C after 2 min of irradiation as measured by insertion of a thermometer in the alumina bath

    Article  CAS  Google Scholar 

  20. Furniss BS, Hannaford AJ, Rogers V, Smith PWG, Tatchell AR (eds) (1978) Vogel’s textbook of practical organic chemistry, 4th edn, p 806

  21. Moriarty RM, Berglund BA, Penmesta R (1992) Tetrahedron Lett 33:6065

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Sam Houston State University, Huntsville, TX, 77341-2117, USA

    Rajender S. Varma, Rajender Dahiya & Dalip Kumar

  2. Texas Regional Institute for Environmental Studies (TRIES), Sam Houston State University, Huntsville, TX, 77341-2117, USA

    Rajender S. Varma

Authors
  1. Rajender S. Varma
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  2. Rajender Dahiya
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  3. Dalip Kumar
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Correspondence to Rajender S. Varma.

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Varma, R.S., Dahiya, R. & Kumar, D. Solvent-Free Oxidation of Benzoins using Oxone on Wet Alumina under Microwave Irradiation. Molecules Online 2, 82–85 (1998). https://doi.org/10.1007/s007830050059

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  • DOI: https://doi.org/10.1007/s007830050059

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