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Anodic Reactions

  • Demetrios Kyriacou
Chapter
Part of the Springer Lab Manual book series (SLM)

Abstract

Anodic or electrooxidative organic reactions generally involve three fundamental intermediates [1,2,7,9,10,11]:
  1. 1.

    Cation radicals, \({R^{\mathop + \limits_ \bullet }}\)

     
  2. 2.

    Radicals, R.

     
  3. 3.

    Cations, R+

     

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References

Section 2.1 Fundamental Nature

  1. 1.
    Yoshida K (1984) Electrooxidation in organic chemistry. Wiley-Interscience, New YorkGoogle Scholar
  2. 2.
    Bard AJ, Ledwith A, Shine H (1976) Adv Phys Org Chem 13: 155Google Scholar
  3. 3.
    Baizer MM, Lund H (eds) (1983) Organic electrochemistry. Marcel-Dekker, New YorkGoogle Scholar
  4. 4.
    Kyriacou D (1981) Basics of electroorganic synthesis. Wiley-Interscience, New YorkGoogle Scholar
  5. 5.
    Kyriacou D, Jannakoudakis D (1986) Electrocatalysis for organic synthesis. Wiley- Interscience, New YorkGoogle Scholar
  6. 6.
    Fry A J (1989) Synthetic organic electrochemistry. Wiley-Interscience, New YorkGoogle Scholar
  7. 7.
    Eberson L (1982) Adv Phys Org Chem 18: 79Google Scholar
  8. 8.
    Eberson L (1987) Electron transfer reactions. Springer, Berlin Heidelberg New YorkGoogle Scholar
  9. 9.
    Ross SD, Finkelstein M, Rudd EJ (1975) Anodic oxidations. Academic press, New YorkGoogle Scholar
  10. 10.
    Uneama K, Steckhan E (eds) (1987) Topics in current chemistry, vol 142. Springer, Berlin Heidelberg New YorkGoogle Scholar
  11. 11.
    Weinberg NL, Weinberg HR (1968) Chem Rev 68: 449Google Scholar

Section 2.2 Hydrocarbons

  1. 1a.
    Pletcher D, Fleischmann M, Korinek K (1971) J Electroanal Chem 33: 478Google Scholar
  2. 1b.
    Clark DB, Fleischmann M, Pletcher D (1972) J Electroanal Chem 36: 137Google Scholar
  3. 1c.
    Bertram J, Coleman JP, Fleischmann M, Pletcher D (1973) J Chem Soc Perkin, Trans 2: 374Google Scholar
  4. 2.
    Coleman JP, and Pletcher D (1974) Tetrahedron Lett 147; Bertram J, Fleischmann M, Pletcher D (1978) Tetrahedron Lett 349Google Scholar
  5. 3.
    Kollmer H, Smith AO (1970) Chem Physics Lett 5: 7Google Scholar
  6. 4.
    Olah GA (1967) J Am Chem Soc 89: 2227Google Scholar
  7. 5.
    Tomat R, Rigo A (1986) J Appl Electrochem 16: 8Google Scholar
  8. 6.
    Nyberg K (1971) Acta Chem Scand 25:534; Fleischmann M, Pletcher D (1969) Tetrahedron Lett 6225; Adams RN (1969) Accounts Chem Res 2:175; Brans K, Mann CK (1967) J Org Chem 32: 1474Google Scholar
  9. 7.
    Dietrich M, Heinze J (1981) Angew Chem 24: 508Google Scholar
  10. 8.
    Mann CK (1969) In: Bard AJ (ed) Electroanalytical chemistry, vol 3. Marcel-Dekker, New YorkGoogle Scholar
  11. 9.
    Steckhan E (1978) J Am Chem Soc 100: 3526Google Scholar
  12. 10.
    Nyberg K (1970) Acta Chem Scand 24: 1609Google Scholar
  13. 11.
    Becker JY, Miller LL, Boekelheide V, Morgan T (1976) Tetrahedron Lett 2939Google Scholar
  14. 12.
    Sato T, Kamada M (1977) J Chem Soc Perkin Trans 2: 384Google Scholar
  15. 13.
    Sainsbury M, Schinazi RE (1972) J Chem Soc Chem Commun 718Google Scholar
  16. 14.
    Kotani E, Tekeuchi N, Tobinaga S (1975) J Chem Soc Chem Commun 550Google Scholar
  17. 15.
    Palmquist V, Nilsson A, Parker VD, Ronlan A (1976) J Am Chem Soc 98: 2571Google Scholar
  18. 16.
    Sainsbury M, Wyatt J (1979) J Chem Soc Perkin Trans 1: 108Google Scholar
  19. 17.
    Miller LL (1979) Pure Appl Chem 51: 2125Google Scholar
  20. 18.
    Piersma BJ (1967) In: Gileadi E (ed) Electrosorption. Plenum Press, New York; Damhs H, Grear M (1963) J Electrochem Soc 110:1075; Bockris JOM ( 1966 ) Modern aspects of electrochemistry. Plenum Press, New York, chap 2Google Scholar
  21. 19.
    Bordaell FC, Cheng JP, Bausch MJ, Bases JE (1988) J Phys Org Chem 1: 208Google Scholar
  22. 20.
    Yoshida K, Nagase S (1979) J Am Chem Soc 101: 4268Google Scholar

Section 2.3 Hydroxy Compounds

  1. 1.
    Lund H (1971) In: Patai S (ed) Chemistry of the hydroxy group. Wiley-Interscience, LondonGoogle Scholar
  2. 2.
    Lund H (1957) Acta Chem Scand 11: 491Google Scholar
  3. 3.
    Parker VD (1978) In: Bard AJ, Lund H (eds) Encyclopedia of electrochemistry. Marcel-Dekker, New York, vol VI, p 181Google Scholar
  4. 4.
    Fleischmann M, Korinek K, Pletcher D (1971) Electroanal Chem 31: 39Google Scholar
  5. 5.
    Vertes G, Horanyi G, Nagg F (1972) Tetrahedron 28: 377Google Scholar
  6. 6.
    Schäfer HJ, Kaulen J (1982) Tetrahedron 38: 3299Google Scholar
  7. 7.
    Kaulen J, Schäfer HJ (1979) Synthesis 513Google Scholar
  8. 8.
    Lund T, Lund H (1984) In: Extended abstracts, vol 84. The Electrochemical Society Cincinnati, Ohio, Abst 330Google Scholar
  9. 9.
    Chum Li H, Ellis KJ, Islam N, Smith CZ, Sopher DW, Utley JHP (1984), Extended abstracts. The Electrochemical Society, Cincinnati, Ohio In: Abst 332Google Scholar
  10. 10.
    Chum Li H, Baizer MM (1985) The electrochemistry of biomass and derived materials. ACS MonographGoogle Scholar
  11. 11.
    Bockris JOM, Piersma BJ, Gileadi E (1964) Electrochim Acta 9: 1329Google Scholar
  12. 12.
    Pletcher D, Fleischmann M, Korinek K (1971) J Electroanal Chem 33: 478Google Scholar
  13. 13.
    Hampton NA, Lee JB, MacDonald KI (1972) Electrochim Acta 19: 921Google Scholar
  14. 14.
    Kyriacou D, Tougas TP (1987) J Org Chem 52: 2318Google Scholar
  15. 15.
    McMillan JA (1962) Chem Rev 62: 65Google Scholar
  16. 16.
    Kyriacou D, University of Massachusetts. Lowell (unpublished work)Google Scholar
  17. 17.
    Ref. 5, section 2.1Google Scholar
  18. 18.
    Kuguni Y, Nonaka T, Bochong Y, Watanaba N (1992) Electrochim Acta 37: 353Google Scholar
  19. 19.
    Sundholm G (1971) J Electrochem Soc 31:265; (1971) Acta Chem Scand 25: 3188Google Scholar
  20. 20.
    Belanger G (1976) J Electrochem Soc 123: 818Google Scholar
  21. 21.
    Scholl PC, Lentsch SE, van de Mark MR (1976) Tetrahedron 32: 303Google Scholar

Section 2.4 Oxide Covered Electrodes

  1. 1.
    Pohl JP, Picket H (1988) In: Trassati S (ed) Electrodes of conductive oxides. Elsevier, New York, p 192Google Scholar
  2. 2.
    Kyriacou D, Janhgen EGE, Tougas TP, University of Massachusetts, Lowell. Siver oxide anodes as biosensors, a. Debenedetto MJ (1991) PhD Thesis; b. DeMott J (1992) PhD ThesisGoogle Scholar
  3. 3.
    Stonehart P, Portandet EP (1968) Electrochim Acta 13: 1805Google Scholar
  4. 4.
    Droog JMM, Huisman F (1980) J Electroanal Chem 15: 211Google Scholar
  5. 5.
    Schäfer HJ, Kaulen J (1982) Tetrahedron 38: 3299Google Scholar
  6. 6.
    Ref. 5, section 2.1Google Scholar
  7. 7.
    Fleischmann M, Korinek K, Pletcher D (1971) J Electroanal Chem 31:97; (1972) J Chem Soc Perkin Trans 2: 1396Google Scholar
  8. 8.
    Fleischmann M, Pletcher D (1973) Adv Phys Org Chem 10:155; Pletcher D, Walsh F (1990) Chem Rev 90: 837Google Scholar
  9. 9.
    Robertson PM (1980) J Electroanal Chem 111: 97Google Scholar
  10. 10.
    Kyriacou D, Tougas TP (1987) J Org Chem 52:2318; Hampton NA, Lee JB, Morley JR, Scanton B (1969) Can J Chem 47: 3789Google Scholar
  11. 11.
    Kyriacou D. University of Massachusetts, Lowell (unpublished work)Google Scholar
  12. 12.
    Bondarenko EG, Tomilov AP Zh (1969) Prikl Khim 42: 2033Google Scholar
  13. 13.
    Campbell KD, Gulbankian AH, Edamura F, Kyriacou D (1985) US patent 4446440Google Scholar
  14. 14.
    Kolb DM (1978) Adv Electrochem Engn 11:125; Jütner K (1986) Electrochim Acta 31:8; Kokkinidis G, Theodoridou E, Jannakoudakis D, University of Thessaloniki, private communications; Adzic RR, Tripkovic AV, Markovic NM (1980) J Electroanal Chem 14:37; Kokkinidis G, Jannakoudakis D (1982) J Electroanal Chem 133: 307Google Scholar
  15. 15.
    Ocon P, Beden B, Huser H, Lamy C (1987) Electrochim Acta 32: 387Google Scholar

Section 2.5 Phenolic Compounds

  1. 1.
    Yoshida K (1984) Electrooxidation in organic synthesis. Wiley-Interscience, New York, p 229Google Scholar
  2. 2.
    Tablem A, Wang S, Swenton JS (1992) J Org Chem 57: 2135Google Scholar
  3. 3.
    Nash RA, Skauen DM, Pardy WC (1958) J Am Pharm Assoc 47: 443Google Scholar
  4. 4.
    Covitz FH (1980) French Patent 154350; Tabakovic I, Gruzic Z, Bejtovic Z (1983) J Heterocyc Chem 20: 635Google Scholar
  5. 5.
    Svanholm V, Bechgaard K, Parker VD (1974) J Am Chem Soc 96: 2409Google Scholar
  6. 6.
    Oyama N, Osaka T, Sazuki T (1987) J Electrochem Soc 134: 3068Google Scholar
  7. 7.
    Torri S, Diminaka AL, Yoshikata A, Inokuchi T (1989) Tetrahedron Lett 30: 2105Google Scholar
  8. 8.
    Smith C, Utley JHP, Petrescu M, Viertier H (1989) J Appl Electrochem 19: 535Google Scholar
  9. 9.
    Lalvani SB, Rajagopal P (1992) J Electrochem Soc 139, No 1Google Scholar
  10. 10.
    Schutte JHP, du Plessis JAK, Lachman G, Vilgoen AM, Nelson AD (1989) J Chem Soc Chem Commun 1290Google Scholar

Section 2.6 Carbonyl Compounds

  1. 1.
    Weinberg NL, Weinberg HR (1968) Chem Rev 68: 449Google Scholar
  2. 2.
    Fedorenko (1974) In: Tipson RS, Horton D (eds) Advances in carbohydrate chemistry and biochemistry. Academic Press, New YorkGoogle Scholar
  3. 3.
    Bockris JOM, Piersma BJ, Gileadi E (1964) Electrochim Acta 9: 1329Google Scholar
  4. 4.
    Chiba T, Okimoto M, Nagai H, Takata Y (1982) Bull Chem Soc (Japan) 55: 335Google Scholar
  5. 5.
    Koch VR, Miller LL (1982) J Electroanal Chem 43: 318Google Scholar
  6. 6.
    Becker JY, Miller LL, Siegel TM (1975) J Am Chem Soc 97: 849Google Scholar
  7. 7.
    Becker JY, Byrd RR, Miller LL, So YH (1975) J Am Chem Soc 97: 853Google Scholar
  8. 8.
    Segura M, Barba F, Aldaz A (1986) Electrochim Acta 31: 83Google Scholar
  9. 9.
    Ye S, Beck F (1991) Tetrahedron 47: 5465Google Scholar
  10. 10.
    Ismail MT (1987) Bull Soc Chim (France) 438Google Scholar
  11. 11.
    Chiba T, Okimoto M (1992) J Org Chem 57: 1375Google Scholar

Section 2.7 Carboxylic Acids

  1. 1.
    Kolbe H (1849) Liebigs Ann 69: 257Google Scholar
  2. 2.
    Utley JHP (1974) In: Weinberg NL (ed) Techniques of electroorganic synthesis part I. Wiley-Interscience, New York, p 793Google Scholar
  3. 3.
    Weedon BCL (1960) Adv Org Chem 1: 1Google Scholar
  4. 4.
    Finkelstein M, Petersen RC (1960) J Org Chem 25: 136Google Scholar
  5. 5.
    Rand L, Mohar AF (1965) J Org Chem 30: 388Google Scholar
  6. 6.
    Conway BE, Vigh AK (1967) Electrochim Acta 12: 102Google Scholar
  7. 7.
    Vasiliev Yu B, Korsman ED, Freiden G (1982) Electrochim Acta 27: 937Google Scholar
  8. 8.
    Einhorn J, Soulser JL, Bucheet C (1983) Can J Chem 61: 584Google Scholar
  9. 9.
    Vasiliev Yu B, Budetzky US, Korsman EP (1982) Electrochim Acta 27: 929Google Scholar
  10. 9a.
    Wladislaw B, Ayers AMJ (1962) J Org Chem 27:281; Coleman JP, Utley JHP, Weedon BCL (1964) J Chem Soc Chem Commun 438Google Scholar
  11. 10.
    Uneama K, Namba H (1988) J Org Chem 53: 4598Google Scholar
  12. 11.
    Pletcher D, Smith CZ (1975) J Chem Soc Perkin Trans 1: 948Google Scholar
  13. 12.
    Ogumi Z, Yamashita H, Nishio K, Takehara Z, Yoshizawa S (1983) Electrochim Acta 28: 1687Google Scholar
  14. 13.
    Kraeutler B, Bard AJ (1978) J Am Chem Soc 99:77; (1978) J Am Chem Soc 100: 2239Google Scholar

Section 2.8 Amines and Amides

  1. 1.
    Lord SS, Rojers LB (1954) Anal Chem 26: 284Google Scholar
  2. 2.
    Nelson RF, Adams RN (1968) J Am Chem Soc 90: 3925Google Scholar
  3. 3.
    Portis LC, Klug TJ, Mann CK (1974) J Org Chem 39: 3488Google Scholar
  4. 4.
    Cauquis G, Fauvelot G, Rigani J (1968) Bull Soc Chim 12: 4928Google Scholar
  5. 5.
    Seo ET, Nelson RF, Fritsch JM, Marcoux LS, Leedy DW, Adams RN (1966) J Am Chem Soc 88: 3498Google Scholar
  6. 6.
    Greason SC, Weeder J, Nelson RF (1972) J Org Chem 37: 4440Google Scholar
  7. 7.
    Barns KK, Mann CK (1967) J Org Chem 32: 1474Google Scholar
  8. 8.
    Smith PJ, Mann CK (1969) J Org Chem 34: 1821Google Scholar
  9. 9.
    Serve D (1976) Electrochim Acta 21: 1171Google Scholar
  10. 10.
    Feldhues V, Schäfer HJ (1982) Synthesis 82: 145Google Scholar
  11. 11.
    Serve D (1975) J Am Chem Soc 97: 432Google Scholar
  12. 12.
    Wawzonek S, Mclntyre T (1967) J Electrochem Soc 114: 1025Google Scholar
  13. 13.
    Esteban PC, Leger JM, Lamy C, Genies E (1989) J Appl Electrochem 19: 462Google Scholar
  14. 14.
    Hand RL, Nelson RF (1978) J Electrochem Soc 125: 1059Google Scholar
  15. 15.
    Lowert BA, Marcoux Y, Bard AJ (1972) J Am Chem Soc 94: 5538Google Scholar
  16. 16.
    Finkelstein M, Nyberg K, Ross SD, Servin R (1978) Acta Chem Scand B32: 182Google Scholar
  17. 17.
    Shono T, Matsumura Y, Tsubata K (1981) J Am Chem Soc 103: 1172Google Scholar
  18. 18.
    Hall LR, Iowamoto RT, Haluznik RP (1989) J Org Chem 54: 2446Google Scholar
  19. 19.
    Rudd EJ, Finkelstein M, Ross SD, Nyberg K, Servin R (1976) Acta Chem Scand B30: 640Google Scholar
  20. 20.
    Bolzan AE, Iwasita T (1988) Electrochim Acta 33: 109Google Scholar
  21. 21.
    Degner D (1989) Dechema-Mon (Org Electrochem) 375Google Scholar
  22. 22.
    Swenton JS, Brian RB, Cung-Pin C, Chun Tzer-C (1989) J Org Chem 54: 51Google Scholar

Section 2.9 Ethers and Esters

  1. 1.
    Ronlan A, Behgaard K, Parker VD (1973) Acta Chem Scand 27: 2375Google Scholar
  2. 2.
    Hammerich O, Moe NS, Parker VD (1972) J Chem Soc Chem Commun 156Google Scholar
  3. 3.
    Svanholm U, Parker VD (1972) Tetrahedron Lett 471Google Scholar
  4. 4.
    Stewart RF, Miller LL (1980) J Am Chem Soc 102: 4999Google Scholar
  5. 5.
    Venkachadan CS et al. (1991) Tetrahedron Lett 51: 7592Google Scholar
  6. 6.
    Shono T, Matsumura Y (1969) J Am Chem Soc 91: 2003Google Scholar
  7. 7.
    Weinberg NL, Beleau B (1973) Tetrahedron 29: 279Google Scholar
  8. 8.
    Koch D, Schafer HJ, Steckhan E (1974) Chem Ber 107: 3640Google Scholar
  9. 9.
    Callot HJ, Louati A, Gross M (1983) Bull Soc Chim 11: 317Google Scholar
  10. 10.
    Moeller KD, Tinao LV (1992) J Am Chem Soc 114: 1033Google Scholar
  11. 11.
    Boyd JW, Schmaltz PW, Miller LL (1980) J Am Chem Soc 162: 3856Google Scholar
  12. 12.
    Miller LL, Ramachandra V (1974) J Org Chem 39: 369Google Scholar
  13. 13.
    Yadav AK, Misra SC (1986) Electrochim Acta 31: 507Google Scholar

Section 2.10 Organic Halides

  1. 1.
    Miller LL, Hoffman AK (1967) J Am Chem Soc 89: 593Google Scholar
  2. 2.
    Laurent A, Laurent E, Tardivel R (1973) Tetrahedron Lett 4861Google Scholar
  3. 3.
    Laurent E, Tardivel R (1976) Tetrahedron Lett 1779Google Scholar
  4. 4.
    Miller LL, Kuzawa E, Campbell CP (1970) J Am Chem Soc 92: 2821Google Scholar
  5. 5.
    Becker JY (1971) J Org Chem 42:3997; Coch VR, Miller LL (1973) Tetrahedron Lett 693Google Scholar
  6. 6.
    German A, Brunei D, Moreau P (1989) J Fluorine Chem 43: 249Google Scholar
  7. 7.
    Becker JY, Smart E, Fukunga T (1988) J Org Chem 53: 5714Google Scholar
  8. 8.
    Hoffender H, Lorch HW, Wendt H (1975) J Electroanal Chem 66: 183Google Scholar

Section 2.11 N-Heterocyclics

  1. 1.
    a. Kwee S, Lund H (1969) Acta Chem Scand B23:2121; b. Weinberg NL, Weinberg HR (1968) Chem Rev 68:449; c. Babbit JM et al. (1966) Chem Ind (London) 2127; d. Eisner V, Kuthan J (1972) Chem Rev 72; e. Kuthan J, Kurfurst A (1982) Ind Eng Chem Proc Res Div 21:191; f. Ludvic J et al. (1987) Electrochim Acta 32:1063; g. Goyal RN et al. (1987) Bull Soc Chim 78Google Scholar
  2. 2.
    Yoshida K (1979) J Am Chem Soc 101:2116; Yoshida K (1978) J Chem Soc Chem Commun 1108Google Scholar
  3. 3.
    Ref. 9, section 2.9Google Scholar
  4. 4.
    Yoshida K, Kitabayshi H (1987) Bull Chem Soc (Japan) 60: 3093Google Scholar
  5. 5.
    Iwasaki T, Horikawa H, Matsumoti K, Mioshi M (1979) J Org Chem 44:1552; Nyberg K (1976) Synthesis, 545Google Scholar
  6. 6.
    Billon JP, Cauquis G, Combrisson J, Li AM (1960) Bull Soc Chim (France) 2062Google Scholar
  7. 7.
    Cauquis G, Falmy HM, Pierre G, Elnagdi MH (1970) J Heterocycl Chem 16: 413Google Scholar
  8. 8.
    Zzochralska B, Elving P (1981) Electrochim Acta 26: 1755Google Scholar
  9. 9.
    Lacoutre F, Barbey G (1983) Electrochim Acta 28: 1617Google Scholar
  10. 10.
    Bellamy AJ, Innes DI (1982) J Chem Soc Perkin Trans 2: 1599Google Scholar
  11. 11.
    Thaning M, Wistrand G (1989) Acta Chem Scand B43: 290Google Scholar
  12. 12.
    Laupp G, Koleli F, Gründen E (1985) Auger Chem 24: 864Google Scholar
  13. 13.
    Wrona MA, Dryhurst G (1988) J Org Chem 54: 2718Google Scholar
  14. 14.
    Anne A, Moiroux J (1988) J Org Chem 53: 2816Google Scholar
  15. 15.
    Cupta PN, Rather GM (1988) J Ind Chem Soc LXV 633Google Scholar
  16. 16.
    Prägst E, Bock C (1975) J Electrochem Soc 61: 47Google Scholar

Section 2.12 Organosulfur Compounds

  1. 1.
    Cottrell PT, Mann CK (1969) J Electrochem Soc 116: 1499Google Scholar
  2. 2.
    Shono T, Matsumara Y, Mizozuch M, Hayashi J (1979) Tetrahedron Lett 3861Google Scholar
  3. 3.
    Jansson R (1984) Chem Eng News 62: 43Google Scholar
  4. 4.
    Cuttler LH (1979) AIChE Symposium Ser 185 75: 103Google Scholar
  5. 5.
    Kimura M, Matsuhara S, Sawaki Y (1984) J Chem Soc Chem Commun 1619Google Scholar
  6. 6.
    Porter DN, Utley JHP (1978) J Chem Soc Chem Commun 255Google Scholar
  7. 7.
    Saeva FD, Morgan BP, Fisher MW, Haley NF (1984) J Org Chem 49: 390Google Scholar
  8. 8.
    Glass RS, Petson A, Wilson G (1986) J Org Chem 51: 4337Google Scholar
  9. 9.
    Uneama K, Torii S (1972) J Org Chem 37: 367Google Scholar
  10. 10.
    Silber JJ, Shine HJ (1971) J Org Chem 36: 2923Google Scholar
  11. 11.
    Kim K, Hull VJ, Shine HJ (1974) J Org Chem 39: 2534Google Scholar
  12. 12.
    Parker VD, Eberson LJ (1970) J Am Chem Soc 92: 7488Google Scholar
  13. 13.
    Ref. 1, section 2.1Google Scholar
  14. 14.
    Hammerich O, Moe NS, Parker VD (1972) J Chem Soc Chem Commun 156Google Scholar

Section 2.13 Anodic Cyanations

  1. 1.
    Nilsson S (1969) Dis Faraday Soc 45: 242Google Scholar
  2. 2.
    Miller LL (1979) Pure App Chem 51: 2125Google Scholar
  3. 3.
    Koyama K, Susuki T, Tsutsumi S (1967) Tetrahedron 23: 2675Google Scholar
  4. 4.
    Andreades S, Zahnow EW (1969) J Am Chem Soc 91: 4181Google Scholar
  5. 5.
    Parker VD, Bargert BE (1965) Tetrahedron Lett 4065Google Scholar
  6. 6.
    Nilsson S (1973) Acta Chem Scand 27: 329Google Scholar
  7. 7.
    Susuki T, Koyama K, Omori A, Tsutsumi S (1968) Bull Chem Soc (Japan) 41: 2663Google Scholar
  8. 8.
    Yoshida K, Nagase S (1979) J Am Chem Soc 101: 4268Google Scholar
  9. 9.
    Papouchado L, Adams RN, Feiberg WS (1969) J Electroanal Chem 21: 408Google Scholar
  10. 10.
    Cauquis G, Serve D (1979) Bull Soc Chim (France) 2: 145Google Scholar
  11. 11.
    Shine JH, Ristagno CV (1972) J Org Chem 37: 3424Google Scholar
  12. 12.
    Nyberg K (1976) Acta Chem Scand 30: 2499Google Scholar
  13. 13.
    March J (1977) Advanced organic chemistry. McGraw-Hill International Student Edition Kagakusha, Ltd. p 503Google Scholar
  14. 14.
    Ref. 20, section 2.2Google Scholar
  15. 15.
    Eberson L, Parker VD (1969) J Chem Soc Chem Commun 340Google Scholar
  16. 16.
    Inoue T, Tsutsumi S (1965) Bull Chem Soc (Japan) 38: 661Google Scholar
  17. 17.
    Nyberg K (1971) Acta Chem Scand 33: 2499Google Scholar
  18. 18.
    Yoshida K (1979) J Am Chem Soc 99: 6111Google Scholar
  19. 19.
    Chiba T, Takata Y (1977) J Org Chem 42: 2973Google Scholar
  20. 20.
    Yoshida K, Fueno T (1970) J Chem Soc Chem Commun 711Google Scholar
  21. 21.
    Eberson L, Helgée B (1978) Acta Chem Scand B32: 313Google Scholar
  22. 22.
    Eberson L, Radner F (1992) Acta Chem Scand 46: 312Google Scholar

Section 2.14 Acetoxylations and Acetamidations

  1. 1.
    Eberson L (1967) J Am Chem Soc 89: 4669Google Scholar
  2. 2.
    Eberson L, Oberrauch E (1981) Acta Chem Scand B35: 193Google Scholar
  3. 3.
    Eberson L, Nyberg K (1966) J Am Chem Soc 88: 1685Google Scholar
  4. 4.
    Nyberg K (1970) Acta Chem Scand B24: 1609Google Scholar
  5. 5.
    Bum Z, Cedheim L, Eberson L (1977) Acta Chem Scand B31: 662Google Scholar
  6. 6.
    Ross SD, Finkelstein M, Petersen RC (1970) J Org Chem 35: 781Google Scholar
  7. 7.
    Ross SD, Finkelstein M, Petersen RC (1964) J Am Chem Soc 86: 4139Google Scholar
  8. 8.
    So YH, Becker JY, Miller LL (1975) J Chem Soc Chem Common 262Google Scholar
  9. 9.
    Shono T, Matsumura Y, Onomura O, Ozaki M, Kazanawa T (1987) J Org Chem 52: 536Google Scholar
  10. 10.
    Hembrok A, Schäfer HJ (1985) Angew Chem Int Ed Eng 24: 1655Google Scholar
  11. 11.
    Clark DB, Fleischmann M, Pletcher D (1973) J Chem Soc Perkin Trans 2: 1578Google Scholar
  12. 12.
    Eberson L, Nyberg K (1966) Tetrahedron Lett 2389Google Scholar
  13. 13.
    Baizer MM, Wagenknecht JH, Monsanto Chemical Co., USAGoogle Scholar
  14. 13a.
    Nyberg K (1969) J Chem Soc Chem Commun 774Google Scholar
  15. 14.
    Hammerich D, Parker VD (1974) J Chem Soc Chem Commun 245Google Scholar
  16. 15.
    Ref. 11, section 2.14Google Scholar
  17. 16.
    Laurent A, Laurent F, Locher P (1975) Electrochim Acta 20: 857Google Scholar
  18. 17.
    Faita G, Fleischmann M, Pletcher D (1970) J Electroanal Chem 25: 455Google Scholar
  19. 18.
    Fleischmann M, Pletcher D (1972) Chem Eng Techn 44: 187Google Scholar
  20. 19.
    Eberson L, Olefsson B (1969) Acta Chem Scand B23: 2355Google Scholar

Section 2.15 Anodic Halogenations

  1. 1.
    Meyers RA (ed) (1992) Encyclopedia of physical science and technology. Academic Press, New York, p 576Google Scholar
  2. 2.
    Childs WV (1982) In: Weinberg NL (ed) Techniques of electroorganic synthesis, vol 5. Wiley-Interscience, New YorkGoogle Scholar
  3. 3.
    O’Sullivan O, Klink EJP, Liu CC, Yeager EB (1985) J Electrochem Soc 132: 2424Google Scholar
  4. 4.
    Drakesmith FG, Hughes DA (1986) J Fluorine Chem 32: 103Google Scholar
  5. 5.
    Matsuda Y, Nishiki T, Sakota N, Nakagua A (1984) Electrochim Acta 29: 35Google Scholar
  6. 6.
    Casalbore G, Mastragostino M, Valchev S (1975) J Electroanal Chem 61: 33Google Scholar
  7. 7.
    Shono T, Matsumura Y, Onomura O, Ozaki M, Kanazawa T (1987) J Org Chem 52: 536Google Scholar
  8. 8.
    Ibvisagic Z, Pletcher D, Brooks WN, Healy KP (1985) J Appl Electrochem 15: 719Google Scholar
  9. 9.
    Takasy Y, Matsuda Y, Shinigu A, Morita M, Saito M ( 1991 ) Chemistry Lett. ( Japan ) 1685Google Scholar
  10. 10.
    Matsuda Y, Hayashi H (1981) Chemistry Lett (Japan) 661Google Scholar
  11. 11.
    Shono T, Matsumura Y, Kalosh S, Ikeda K, Kamota T (1989) Tetrahedron Lett 30: 1649Google Scholar
  12. 12.
    Miller LL, Watkins BF (1976) J Am Chem Soc 98:1515; Lines R, Parker VD (1980) Acta Chem Scand B34: 47Google Scholar

Section 2.16 Hydroxylations

  1. 1.
    Ronlan A (1971) J Chem Soc Chem Commun 1643Google Scholar
  2. 2.
    Nilsson A, Ronlan A, Parker VD (1973) J Chem Soc Perkin Trans 1: 2337Google Scholar
  3. 3.
    Fremery M, Höver H, Schwartzlose G (1974) Chem Ing Tech 46: 635Google Scholar
  4. 4.
    Majeski EJ, Stuart JD, Obnesoge WE (1968) J Am Chem Soc 90: 633Google Scholar
  5. 5.
    Parker VD (1970) Acta Chem Scand B24: 2757Google Scholar
  6. 6.
    Sternerup H (1974) Acta Chem Scand B28: 579Google Scholar
  7. 7.
    Ponsold K, Kash H (1979) Tetrahedron Lett 4463Google Scholar
  8. 8.
    Steckhan E, Schäfer HJ (1974) Angew Chem 13: 472Google Scholar

Section 2.17 Alkoxylations

  1. 1.
    Inoue T et al. (1963) Tetrahedron Lett 1409Google Scholar
  2. 2.
    Couture R, Beleaw B (1972) Can J Chem 50: 3424Google Scholar
  3. 3.
    Brettle R, Sutton JR (1975) J Chem Soc Perkin Trans 1: 1947Google Scholar
  4. 4.
    Engles R, Schäfer HJ, Steckhan E (1977) Justus Liebigs Ann Chem 204Google Scholar
  5. 5.
    Kim HJ, Kusabak K, Hokazono S, Morooka S, Kato S (1987) J Appl Electrochem 17: 1213Google Scholar
  6. 6.
    Shono T, Matsumura Y (1970) J Org Chem 35: 4157Google Scholar
  7. 7.
    Brettle R, Sutton JR (175) J Chem Soc Perkin Trans 1:1955Google Scholar
  8. 8.
    Manning MJ, Raynolds PW, Swenton JS (1976) J Am Chem Soc 98: 5008Google Scholar
  9. 9.
    Jackson DK, Swenton JS (1977) Synth Commun 7: 333Google Scholar
  10. 10.
    Yoshida J, Murata T, Isoe S (1987) Tetrahedron Lett 28: 211Google Scholar
  11. 11.
    Shono T, Matsumura Y, Tsubaka K (1981) J Am Chem Soc 103: 1172Google Scholar
  12. 12.
    Palmquist V, Nilsson A, Ronlan A, Parker VD (1979) J Org Chem 44: 196Google Scholar
  13. 13.
    Warning K, Mitzlaff M, Jensen H (1978) Justus Liebigs Ann Chem Ann Chem 1707Google Scholar
  14. 14.
    Shono T, Matsumura Y (1969) J Am Chem Soc 91: 2803Google Scholar
  15. 15.
    Goosens HJM, Top AWH (1978) Synthesis 283Google Scholar
  16. 16.
    Weinberg NL, Brown EA (1966) J Org Chem 31: 4054Google Scholar
  17. 17.
    Rudd EJ, Finkelstein M, Ross DS (1972) J Org Chem 37: 1763Google Scholar
  18. 18.
    Barba I, Chincilla, R, Gomez C (1991) J Org Chem 56, 3673Google Scholar
  19. 19.
    Weinberg NL, Weinberg HR (168) Chem Rev 471Google Scholar
  20. 20.
    Barba I, Alonso F (1989) J Org Chem 54: 4365Google Scholar
  21. 21.
    Nilsson A, Palmquist V, Peterson T, Ronlan A (1978) J Chem Soc Perkin Trans 1: 708Google Scholar
  22. 22.
    Shono T, Ikeda A, Kimura T (1971) Tetrahedron Lett 3599; Margaretha P, Tissol P (1975) Helv Chim Acta 58: 933Google Scholar
  23. 23.
    Dolson MG, Swenton JS (1981) J Org Chem 46: 177Google Scholar
  24. 24.
    Dolson MG, Swenton JS (1981) J Am Chem Soc 103: 2361Google Scholar

Section 2.18 Pyridinations

  1. 1.
    Parker VD, Eberson L (1970) Acta Chim Scand B24:3542; Blackman GM, Will JP (1974) J Chem Soc Chem Commun 67; Yoshida K, Nagasi S (1979) J Am Chem Soc 101: 4268Google Scholar
  2. 2.
    Manning G, Parker VD, Adams RN (1969) J Am Chem Soc 91: 7584Google Scholar
  3. 3.
    Blount HN, Kuwana T (1973) J Electroanal Chem 27: 271Google Scholar

Section 2.19 Nitrations

  1. 1.
    Achord JM, Hussey C (1981) J Electrochem Soc 128: 2556Google Scholar
  2. 2.
    Kargin Yu M (1987) J Gen Chem (USSR) 56: 1863Google Scholar
  3. 3.
    Bloom AJ, Fleischmann M, Mellor JM (1987) Electrochim Acta 32: 785Google Scholar
  4. 4.
    Eberson L, Radner F (1986) Acta Chem Scand B40: 71Google Scholar
  5. 5.
    Laurent A, Laurent E, Locher P (1975) Electrochim Acta 20: 857Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1994

Authors and Affiliations

  • Demetrios Kyriacou
    • 1
  1. 1.Department of ChemistryUniversity of MassachusettsLowellUSA

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