Skip to main content
SpringerLink
Log in

Description of catalyzed and induced (initiated) reactions of organic compounds. Terminology problems

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The fundamental differences between catalyzed and induced (initiated) reactions and some terminological problems that exist in this field are considered. In particular, illegitimacy of using terms such as “catalytically induced (initiated) reactions”, “expendable catalystrd, and “catalytic additive” is discussed. For non-catalyzed transformations, including conjugated (in particular, multicomponent) and chain reactions, the term self-developing reaction (SDR) is proposed. The criterion of SDR is a high current yield (electrogeneration) or high quantum yield (photoinitiation) of target products; in the case of chemical induction of SDR, a substantially lower consumption of the inductor than required by the reaction stoichiometry can serve as such criterion.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Khimicheskaya Entsiklopediya [Chemical Encyclopedia], Nauch. izd-vo Bol’shaya rossiiskaya entsiklopediya, Moscow, 1998, Vol. 5, p. 346, column 683 (in Russian).

  2. IUPAC Compendium of Chemical Terminology — the Gold Book, Version 2.3.2. 2012-08-19; http://gold.book.iupac.org.

  3. Nomenklaturnye Pravila IYuPAK po Khimii [IUPAC Nomenclature Rules in Chemistry], Physical Organic Chemistry, Moscow, 1985, Vol. 5 (in Russian).

  4. Glossary of Terms Used in Physical Organic Chemistry (IUPAC recommendations 1994), Pure Appl. Chem., 1994, 66, 1077; http://www.iupac.org/publications/pac/1994/pdf/6605x1077.pdf.

  5. N. M. Emanuel’, D. G. Knorre, Kurs Khimicheskoi Kinetiki [Course on Chemical Kinetics], Vysshaya shkola, Moscow, 1984, p. 309 (a), 349 (b) (in Russian).

    Google Scholar 

  6. L. Tietze, G. Brasche, K. M. Gericke, Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim, 2006, 617 pp.

    Book  Google Scholar 

  7. V. A. Smit, A. D. Dil’man, Osnovy Sovremennogo Organicheskogo Sinteza [Foundations of Modern Organic Synthesis], Binom. Laboratoriya znanii, Moscow, 2009, 750 pp. (in Russian).

    Google Scholar 

  8. M. B. Smith, J. March, March’s Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, 6th ed., J. Wiley, New York—Weinheim, 2007, 2357 pp.

  9. O. A. Reutov, A. L. Kurts, K. P. Butin, Organicheskaya Khimiya [Organic Chemistry], Binom. Laboratoriya znanii, Moscow, 2012, Vols 1–4 (in Russian).

    Google Scholar 

  10. Organic Electrochemistry, 4th ed., Eds H. Lund, O. Hammerich, Marcel Dekker, New York—Basel, 2001, p. 1163 (a); p. 1227 (b).

    Google Scholar 

  11. Khimicheskaya Entsiklopediya [Chemical Encyclopedia], Sov. entsiklopediya, Moscow, 1990, Vol. 2, p. 335, column 662 (in Russian).

  12. Organic Electrochemistry, Ed. M. Baizer, Marcel Dekker, New York, 1974.

    Google Scholar 

  13. E. I. Karpeiskaya, L. S. Gorshkova, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1970, 19, 2556 [Izv. Akad. Nauk SSSR. Ser. Khim., 1970, 2716].

    Article  Google Scholar 

  14. E. I. Karpeiskaya, Yu. N. Kukushkin, V. A. Trofimov, I. D. Ratner, D. P. Shashkin, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1974, 23, 307 [Izv. Akad. Nauk SSSR. Ser. Khim., 1974, 338].

    Article  Google Scholar 

  15. G. V. Isagulyants, A. A. Greish, V. M. Kogan, Kinet. Katal., 1987, 28, 243 [Kinet. Catal. (Engl. Transl.), 1987, 28].

    CAS  Google Scholar 

  16. G. V. Isagulyants, A. A. Greish, V. M. Kogan, G. M. V’yunova, G. V. Antoshin, Kinet. Katal., 1987, 28, 632 [Kinet. Catal. (Engl. Transl.), 1987, 28].

    CAS  Google Scholar 

  17. B. A. Cheskis, Ya. I. Isakov, A. V. Novikov, A. M. Moiseen- kov, Kh. M. Minachev, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1990, 39, 809 [Izv. Akad. Nauk SSSR. Ser. Khim., 1990, 902].

    Article  Google Scholar 

  18. Kh. M. Minachev, Izbrannye Trudy. Geterogennyi Kataliz. Neftekhimiya. Kataliticheskii Organicheskii Sintez [Heterogeneous Catalysis. Petrochemistry. Catalytic Organic Synthesis]. Comp., Ed. N. Ya. Usachev, Librokom, Moscow, 2011, 880 pp. (in Russian).

  19. J. Bougault, E. Catelain, P. Shabrier, Bull. Soc. Chim. France, 1940, 7, 780.

    CAS  Google Scholar 

  20. V. duVignon, D. B. Melville, K. Folkers, D. E. Wolf, R. Mozingo, J. C. Kerestesy, S. A. Harris, J. Biol. Chem., 1942, 146, 475; Chem. Abstr., 1943, 37, 1716.

    Google Scholar 

  21. Novye Napravleniya Khimii Tiofena [New Trends in Thiophene Chemistry], Ed. Ya. L. Gol’dfarb, Nauka, Moscow, 1976, p. 256 (in Russian).

    Google Scholar 

  22. L. I. Belen’kii, V. P. Gul’tyai, Chem. Heterocycl. Compd. (Engl. Transl.), 1981, 17, 523 [Khim. Geterotsikl. Soedin., 1981, 723].

    Article  Google Scholar 

  23. L. I. Belen’kii, Ya. L. Gol’dfarb, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1984, 33, 178 [Izv. Akad. Nauk SSSR. Ser. Khim., 1984, 199].

    Article  Google Scholar 

  24. L. I. Belen’kii, Ya. L. Gol’dfarb, in Thiophene and its Derivatives, Ed. S. Gronowitz, J. Wiley, New York—Chichester—Brisbane—Toronto—Singapore, 1985, Part 1, p. 457.

  25. G. Sartori, R. Maggi, Advances in Friedel—Crafts Acylation Reactions, CRC Press, Boca Raton, 2010, p. 33.

    Google Scholar 

  26. L. I. Belen’kii, A. P. Yakubov, I. A. Bessonova, Zh. Org. Khim., 1977, 13, 364 [J. Org. Chem. USSR (Engl. Transl.), 1977, 13, No. 2].

    Google Scholar 

  27. Problemy Electrokataliza [Problems of Electrocatalysis], Ed. V. S. Bagotskii, Nauka, Moscow, 1980, 271 pp. (in Russian).

    Google Scholar 

  28. Elektrodnye Protsessy v Rastvorakh Organicheskikh Soedinenii [Electrode Processes in Solutions of Organic Compounds], Ed. B. B. Damaskin, izd-vo MGU, Moscow, 1985, 311 pp. (in Russian).

    Google Scholar 

  29. I. V. Kirilyus, Elektrokataliticheskoe gidrirovanie organicheskikh soedinenii [Electrocatalytic Hydrogenation of Organic Compounds], Nauka, Alma-Ata, 1990, 124 pp. (in Russian).

    Google Scholar 

  30. L. M. Korotaeva, T. Ya. Rubinskaya, in Focus on Electrochemistry Research, Ed. M. Nuńes, Nova Sci. Publ. Inc., New York, 2005, p. 145.

  31. Electrochemical Dictionary, Eds A. J. Bard, G. Inzelt, F. Scholz, SDRinger-Verlag, Berlin, 2008, p. 77.

    Google Scholar 

  32. N. Isambert, M. del Mar Sanchez Duque, J.-C. Plaquevent, Y. G’enisson, J. Rodriguez, T. Constantieux, Chem. Soc. Rev., 2011, 40, 1347.

    Article  CAS  Google Scholar 

  33. J. P. Hallett, T. Welton, Chem. Rev., 2011, 111, 3508.

    Article  CAS  Google Scholar 

  34. S. G. Zlotin, G. V. Kryshtal, G. M. Zhdankina, A. S. Kucherenko, A. V. Bogolyubov, D. E. Siyutkin, Pure Appl. Chem., 2009, 81, 2059.

    Article  CAS  Google Scholar 

  35. R. Giernoth, Angew. Chem., Int. Ed., 2010, 49, 2834.

    Article  CAS  Google Scholar 

  36. D. E. Pearson, H. W. Pope, J. Org. Chem., 1956, 21, 381.

    Article  CAS  Google Scholar 

  37. D. E. Pearson, H. W. Pope, W. W. Hargrove, W. E. Stamper, J. Org. Chem., 1958, 23, 1412.

    Article  CAS  Google Scholar 

  38. L. I. Belen’kii, E. D. Lubuzh, N. D. Chuvylkin, Russ. Chem. Bull. (Engl. Transl.), 1996, 45, 2717 [Izv. Akad Nauk. Ser. Khim., 1996, 2866].

    Article  Google Scholar 

  39. Ya. L. Gol’dfarb, Yu. B. Vol’kenshtein, Dokl. Akad. Nauk SSSR, 1959, 536 [Dokl. Chem. (Engl. Transl.), 1959, 128, No. 3].

    Google Scholar 

  40. L. I. Belen’kii, G. P. Gromova, Ya. L. Gol’dfarb, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1967, 16, 1573 [Izv. Akad. Nauk. SSSR. Ser. Khim., 1967, 1627].

    Article  Google Scholar 

  41. Ja. L. Goldfarb, Ju. B. Volkenstein, L. I. Belenkij, Angew. Chem., Int. Ed., 1968, 7, 519.

    Article  CAS  Google Scholar 

  42. O. N. Temkin, Gomogennyi Metallokompleksnyi Kataliz. Kineticheskie Aspekty [Homogeneous Metal Complex Catalysis. Kinetic Aspects], Akademkniga, Moscow, 2008, p. 20 (in Russian).

    Google Scholar 

  43. A. Nakamura, M. Tsutsui, Principles and Applications of Homogeneous Catalysis, Wiley, New York, 1980, 204 pp.

    Google Scholar 

  44. V. P. Ananikov, K. A. Gayduk, N. V. Orlov, I. P. Beletskaya, V. N. Khrustalev, M. Yu. Antipin, Chem. Eur. J., 2010, 16, 2063.

    Article  CAS  Google Scholar 

  45. J. Simonet, in Organic Electrochemistry, Eds M. Baizer, H. Lund, Marcel Dekker, New York, 1983, p. 1051.

  46. J. Delunay, M. Orlic-Le, J. Simonet, New. J. Chem., 1993, 17, 393.

    Google Scholar 

  47. V. P. Gul’tyai, A. S. Mendkovich, Ros. Khim. Zh., 2005, 49, No. 5, 40 [Mendeleev Chem. J. (Engl. Transl.), 2005, 49, No. 5].

    Google Scholar 

  48. A. I. Rusakov, A. S. Mendkovich, V. P. Gul’tyai, V. Yu. Orlov, Struktura i Reaktsionnaya Sposobnost’ Organicheskikh Anion-Radikalov [Structure and Reactrivity of Organic Radical Anions], Mir, Moscow, 2005, ch. 5 (in Russian).

    Google Scholar 

  49. V. P. Gul’tyai, XVIII Mendeleevskii s’ezd po obshchei i prikladnoi khimii [XVIII Mendeleev Congress on General and Applied Chemistry] (Moscow, September 23–28, 2007), Abstrs, Moscow, 2007, 1, p. 339 (in Russian).

    Google Scholar 

  50. V. P. Gul’tyai, V Ukrainskii mezhdunar. s’ezd po elektrokhimii [V Ukrainian Int. Congress on Electrochemistry] (Chernovtsy, October 20–24, 2008), Abstrs, Vestnik natsional’nogo tekhnicheskogo universiteta KhPI, 2008, No. 15, 39 (in Russian).

    Google Scholar 

  51. A. A. Zemtsov, V. V. Levin, A. D. Dilman, Eur. J. Org. Chem., 2010, 6779.

    Google Scholar 

  52. Ch. Amatore, A. Jutand, G. Le Duc, Chem. Eur. J., 2011, 17, 2492.

    Article  CAS  Google Scholar 

  53. A. Ananikov, I. Beletskaya, Organometallics, 2012, 31, 1595.

    Article  CAS  Google Scholar 

  54. V. P. Ananikov, K. A. Gayduk, I. P. Beletskaya, V. N. Khrustalev, M. Yu. Antipin, Eur. J. Inorg. Chem., 2009, 1149.

    Google Scholar 

  55. P.-P. Fang, A. Jutand, Z.-Q. Tian, C. Amatore, Angew. Chem., Int. Ed., 2011, 50, 12184.

    Article  CAS  Google Scholar 

  56. Ch. Amatore, Abstr. of 63rd Annu. Meeting Intern. Soc. Electrochem. (Prague, Czech Republic, August 14–24, 2012), Prague, 2012.

    Google Scholar 

  57. K. F. Reid, Properties and Reactions of Bonds in Organic Molecules, Longmans, London, 1968, 556 pp.

    Google Scholar 

  58. O. N. Chupakhin, V. N. Charushin, H. C. van der Plas, Nucleophilic Aromatic Substitution of Hydrogen, Acad. Press, New York, 1994, 367 pp.

    Google Scholar 

  59. V. A. Petrosyan, Mendeleev Commun., 2011, 21, 115.

    Article  CAS  Google Scholar 

  60. V. A. Petrosyan, Aktual’nye problemy elektrokhimii organicheskikh soedinenii, VII Vseros. shkola ECOC-2012 [Topical Problems of Electrochemistry of Organic Compounds. VII All-Russian School ECOC-2012] (Tambov, October 20–25, 2012), Abstrs., FGOU VPO TGTU, p. 20 (in Russian).

  61. J. F. Bunnett, Acc. Chem. Res., 1978, 11, 413.

    Article  CAS  Google Scholar 

  62. R. A. Rossi, R. H. de Rossi, Aromatic Substitution by the SRN1 Mechanism, ACS, Washington, 1983, 300 pp.

    Google Scholar 

  63. Ya. L. Gol’dfarb, A. P. Yakubov, L. I. Belen’kii, Chem. Heterocycl. Compd. (Engl. Transl.), 1979, 15, 853 [Khim. Geterotsikl. Soedin., 1979, 1044].

    Article  Google Scholar 

  64. J. Pinson, J.-M. Saveant, J. Am. Chem. Soc., 1978, 100, 1506.

    Article  CAS  Google Scholar 

  65. M. A. Syroeshkin, L. V. Mikhalchenko, M. Yu. Leonova, A. S. Mendkovich, A. I. Rusakov, V. P. Gul’tyai, Mendeleev Commun., 2011, 21, 26.

    Article  CAS  Google Scholar 

  66. R. G. Scamehorn, J. F. Bunnett, J. Org. Chem., 1977, 42, 1449.

    Article  CAS  Google Scholar 

  67. T. Shono, N. Kise, T. Surumoto, J. Org. Chem., 1985, 50, 2527.

    Article  CAS  Google Scholar 

  68. M. E. Nyazimbetov, D. N. Evans, J. Electrochem. Soc., 1995, 142, 2655.

    Article  Google Scholar 

  69. M. E. Niyazymbetov, L. D. Konyushkin, Z. I. Niyazymbetova, V. P. Litvinov, V. A. Petrosyan, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1991, 40, 240 [Izv. Akad. Nauk SSSR. Ser. Khim., 1991, 260].

    Article  Google Scholar 

  70. V. P. Gul’tyai, XIX Mendeleevskii s’ezd (XIX Mendeleev Congress) (Volgograd, September 25–30, 2011.), Abstrs, Volgograd, 2011, 1, 57 (in Russian).

    Google Scholar 

  71. V. P. Gul’tyai, Aktual’nye problemy elektrokhimii organicheskikh soedinenii, VII Vseros. shkola ECOC-2012 [Topical Problems of Electrochemistry of Organic Compounds. VII All-Russian School ECOC-2012] (Tambov, October 20–25, 2012.), Abstrs, FGOU VPO TGTU, p. 38 (in Russian).

  72. A. I. Ilovaisky, V. M. Merkulova, M. N. Elinson, G. I. Nikishin, Russ. Chem. Rev., 2012, 81, 381.

    Article  CAS  Google Scholar 

  73. A. M. Shestopalov, Y. M. Emeliyanova, A. A. Shestopalov, L. A. Rodinovskaya, D. N. Evans, Tetrahedron, 2003, 59, 7491.

    Article  CAS  Google Scholar 

  74. M. N. Elinson, A. S. Dorofeev, A. I. Ilovaisky, S. K. Feducovich, P. A. Belyakov, G. I. Nikishin, Adv. Synth. Catal., 2008, 350, 591.

    Article  CAS  Google Scholar 

  75. A. N. Nesmeyanov, N. A. Nesmeyanov, Nachala Organicheskoi Khimii [Foundations of Organic Chemistry], Khimiya, Moscow, Book 2, p. 562 (in Russian).

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. P. Gul’tyai & L. I. Belen’kii

Authors
  1. V. P. Gul’tyai
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. L. I. Belen’kii
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. P. Gul’tyai.

Additional information

Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 60th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2279–2291, Novemer, 2013.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gul’tyai, V.P., Belen’kii, L.I. Description of catalyzed and induced (initiated) reactions of organic compounds. Terminology problems. Russ Chem Bull 62, 2279–2290 (2013). https://doi.org/10.1007/s11172-013-0330-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-013-0330-8

Key words

Search

Navigation