Skip to main content
Log in

Synthesis and efficiency of photolysis of methylated 2-dialkylamino- and 2-piperidino-1,4-naphthoquinones

  • Organic Chemistry
  • Reactivity Of Organic Compounds
  • Published:
Bulletin of the Russian Academy of Sciences, Division of chemical science Aims and scope

Abstract

2-Dialkylamino- and 2-piperidino-1,4-naphthoquinones with a methyl group in position 3 or 5(8) of the naphthoquinone were synthesized by reacting dimethyl- and diethylamines and piperidine with 2- and 5-methyl-1,4-naphthoquinones. The quantum yields of photoconversion of the synthesized compounds in benzene were determined. A 1.2- to 6.5-fold increase of the quantum yield over that of 2-dimethylamino-1,4-naphthoquinone was established. A comparison of the quantum yields with the calculated charges on the reaction centers in the excited (T 1) state showed that there is not a linear relationship between them.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. V. N. Berezhnaya, R. P. Shishkina, N. V. Pavlova, et al.,Izv. Akad. Nauk, Ser. Khim., No. 3, 657 (1990).

  2. US Patent No. 4,684,599;RZhKhim., 9N294P (1988).

  3. N. P. Gritsan and N. M. Bazhin,Izv. Akad. Nauk, Ser. Khim., No. 2, 280 (1981).

  4. N. P. Gritsan and N. M. Bazhin,Izv. Akad. Nauk, Ser. Khim., No. 6, 1275 (1980).

  5. H. J. Kallmayer and Ch. Tappe,Arch. Pharm. (Weinheim) 319, 607 (1986).

    Google Scholar 

  6. V. A. Koptyug (ed.),Atlas of Spectra of Aromatic and Heterocyclic Compounds [in Russian], No. 22, NIOKh Sib. Otd.Akad. Nauk, Novosibirsk (1982), p. 60.

    Google Scholar 

  7. USSR Inventor's Certificate, No. 1,181,267;Byull. Izobret., No. 38, 284 (1987).

    Google Scholar 

  8. R. G. Cooke, B. Dowd, and W. Segal,Austral. J. Chem. 6, 38 (1953).

    Google Scholar 

  9. G. Hofle,Tetrahedron 33, No. 15, 1963 (1977).

    Google Scholar 

  10. T. A. Stavitskaya, A. D. Bukhtoyarova, R. P. Shishkina, et al.,Khim. Vys. Energ. 25, No. 3, 262 (1991).

    Google Scholar 

  11. N. M. Émanuél and M. G. Kuzmin (eds.),Experimental Methods of Chemical Kinetics [in Russian], Izd-vo MGU, Moscow (1985), p. 262.

    Google Scholar 

  12. A. A. Bliznyuk, A. A. Voityuk, and L. N. Shchegoleva,Information Materials of SFKP Sib. Otd. Akad. Nauk [in Russian], No. 3, IKhKiG, Novosibirsk (1989).

    Google Scholar 

  13. S. Patai (ed.),The Chemistry of the Quinonoid Compounds, Part 1, London (1974), p. 12.

  14. R. Fletcher and M. J. D. Powell,Comput. J. 6, No. 2, 163 (1963).

    Google Scholar 

  15. A. N. Grinev, I. A. Zaitsev, N. K. Venevtseva, and A. P. Terent'ev,Zh. Obshch. Khim. 30, No. 6, 1914 (1960).

    Google Scholar 

  16. A. H. Crosby and R. E. Lutz,J. Am. Chem. Soc. 78, No. 6, 1233 (1956).

    Google Scholar 

Download references

Authors

Additional information

Institute of Organic Chemistry, Russian Academy of Sciences, Siberian Branch, 630090 Novosibirsk. Translated from Izvestiya Akademii Nauk, Seriya Khimicheskaya, No. 3, pp. 707–714, March, 1992.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Russkikh, V.V. Synthesis and efficiency of photolysis of methylated 2-dialkylamino- and 2-piperidino-1,4-naphthoquinones. Russ Chem Bull 41, 555–561 (1992). https://doi.org/10.1007/BF00863084

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00863084

Keywords

Navigation