Electroorganic Synthesis in Oil-in-Water Nanoemulsion: TEMPO-Mediated Electrooxidation of Amphiphilic Alcohols in Water

Abstract

Oil-in-water nanoemulsions, consisting of TEMPO, amphiphilic alcohols, and water, offer unique reaction environments for electrooxidation of the alcohols to give the corresponding ­carboxylic acids in good to excellent yields.

Key words

electrooxidation - alcohols - nanostructure - TEMPO - aqueous environment

References and Notes

• 1 Osborne DW. Middleton CA. Rogers RL. J. Disp. Sci. Technol.  1988,  9:  415 
• 2a Tiwari SB. Amiji MM. In Nanotechnology for Cancer Therapy   Amiji MM. CRC Press LLC; Boca Raton: 2007.  p.723 
• 2b Chepurnov AA. Bakulina LF. Dadaeva AA. Ustinova N. Chepurnova TS. Baker JR. Acta Tropica  2003,  87:  315 
• 3 Yilmaz E. Borchert H.-H. Int. J. Pharm.  2006,  307:  232 
• 4 Shi X, and Wang Y. inventors; Chinese Patent CN  1873093.  ; Chem. Abstr. 2006, 146, 83440
• 5 Guiramand C. inventors; EP  1634567.  ; Chem. Abstr. 2006, 144, 298822
• 6 Myc A. Vanhecke T. Landers JJ. Hamouda T. Baker JR. Mycopathologia  2002,  155:  195 
• 7 Kesisoglou F. Panmai S. Wu Y. Curr. Nanosci.  2007,  3:  183 
• A few reports dealing with electrolysis in emulsion were published:
• 8a Wadhawan JD. Marken F. Compton RG. Bull SD. Davies SG. Chem. Commun.  2001,  87 
• 8b Atobe M. Chen P.-C. Nonaka T. Electrochemistry (Tokyo)  1998,  66:  556 
• 8c Chen P.-C. Nonaka T. Electrochemistry (Tokyo)  1995,  63:  395 
• 8d Burzyk J. Zjawiony I. Pol. J. Appl. Chem.  1993,  37:  99 
• 8e Chen P.-C. Chang P.-C. Kunugi Y. Nonaka T. Electrochemistry (Tokyo)  1993,  61:  866 
• 8f Georges J. Desmettre S. Electrochim. Acta  1986,  31:  1519 
• 9 Semmelhack MF. Chou CS. Cortes DA. J. Am. Chem. Soc.  1983,  105:  4492 
• 10 Inokuchi T. Matsumoto S. Torii S. J. Org. Chem.  1991,  56:  2416 
• 11 Tanaka H. Kawakami Y. Goto K. Kuroboshi M. Tetrahedron Lett.  2001,  41:  445 
• 12a Kubota J. Ido T. Kuroboshi M. Tanaka H. Uchida T. Shimamura K. Tetrahedron  2006,  62:  4769 
• 12b Tanaka H. Kubota J. Itogawa S. Ido T. Kuroboshi M. Shimamura K. Uchida T. Synlett  2003,  951 
• 13 Water-soluble N-oxyl compounds having hydrophilic ionic parts such as quaternary ammonium moiety and lipophilic alkyl chains work as a mediator as well as an emulsifier to make an oil-in-water microemulsion. Kubota J. Shimizu Y. Mitsudo K. Tanaka H. Tetrahedron Lett.  2005,  46:  8975 
• 14 Schnatbaum K. Schäfer HJ. Synthesis  1999,  864 

15

Theoretical amounts of the electricity are 4 F/mol and 8 F/mol for mono-ols (1a-c) and diols (1d,e), respectively; 1 F = 96500 C.