Skip to main content
SpringerLink
Log in

Raney nickel reductions—Part I

  • Published:
Proceedings of the Indian Academy of Sciences - Section A Aims and scope Submit manuscript

Summary

Treatment of sulphur-containing heterocyclic compounds such as thiodiphenylamine (I) and benzidine-sulphone (II) with Raney nickel in a suitable solvent gave the sulphur-free compounds diphenylamine and N∶N′-diethylbenzidine (reduction in ethyl alcohol).

β-Naphthol gave a mixture of 1∶2∶3⪉-tetrahydro-2-naphthol and 5∶6∶7∶8-tetrahydro-2-naphthol on reduction with Raney nickel in alcoholic alkaline solution. Naphthol AS (2-hydroxy-3-naphthanilide) yielded 5∶6∶7∶8-tetrahydro-2-hydroxy-3-naphthanilide and J-acid gave 6-amino-1-naphthol on treatment with Raney nickel.

Carbazole was unaffected when treated with Raney nickel in morpholine, but gave tetrahydrocarbazole when reduced in alcohol. 3-Chloro- and 3-aminocarbazole also gave tetrahydrocarbazole on reduction in alcohol and dioxan respectively.

Anthraquinone and 2-methylanthraquinone gave octahydro-derivatives on reduction in alcohol. Reduction in morpholine and in aqueous alkali gave several reduction products which are under investigation.

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. Covert and AdkinsJ. A. C. S., 1932,54, 4116.

    Article  Google Scholar 

  2. Spring and BaxterAnnual Rep., 1945,42, 101.

    Google Scholar 

  3. Bougaultet al. Bull. Soc. Chim., 1938,5, 1699; 1940,7, 781.

    Google Scholar 

  4. Mozingoet al. J. A. C. S., 1943,65, 1013.

    Article  Google Scholar 

  5. Wolfrom and KarabinosIbid.,, 1944,66, 909. Sofferet al. Ibid., J. A. C. S., 1945,67, 1435.

    Article  Google Scholar 

  6. Mozingoet al. Ibid.,, 1944,66, 1859.

    Article  Google Scholar 

  7. Papaet al. J. Org. Chem., 1942,7, 587; 1944,9, 1; 1945,10, 232.

    Article  Google Scholar 

  8. V. du. Vigneaudet al. J. Biol. Chem., 1942,146, 475.

    Google Scholar 

  9. Gilman and BroadbentJ. A. C. S., 1947,69, 2053.

    Article  Google Scholar 

  10. See following and subsequent papers.

  11. Adkins and KrsekJ. A. C. S., 1948,70, 412.

    Article  Google Scholar 

  12. Schröter and BayerD. R. P., 629, 698.

  13. SchroeterAnnalen, 1922,426, 147.

    Google Scholar 

  14. Arnoldet al. J. A. C. S., 1941,63, 1314.

    Article  Google Scholar 

  15. von Braun and RitterBer., 1922,55, 3792. von Braun and SchoringIbid., Ber., 1925,58, 2156.

    Google Scholar 

  16. Adkins and CoonradtJ. A. C. S., 1941,63, 1563.

    Article  Google Scholar 

  17. Bamberger and TichivinskyBer., 1902,35, 4182.

    Google Scholar 

  18. SanderIbid.,, 1925,58, 829.

    Google Scholar 

  19. HeilbronDictionary of Organic Compounds, 1943,3, 698.

    Google Scholar 

  20. Bamberger and LodterBer., 1890,23, 211.

    Google Scholar 

  21. Perkin and PlantJ. C. S., 1921,119, 1825.

    Google Scholar 

  22. SkitaBer., 1925,58, 2692.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemical Technology, University of Bombay, India

    K. H. Shah, B. D. Tilak & K. Venkataraman F.A.Sc.

Authors
  1. K. H. Shah
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. B. D. Tilak
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. Venkataraman F.A.Sc.
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shah, K.H., Tilak, B.D. & Venkataraman, K. Raney nickel reductions—Part I. Proc. Indian Acad. Sci. (Math. Sci.) 28, 142 (1948). https://doi.org/10.1007/BF03170785

Download citation

  • Received:

  • DOI: https://doi.org/10.1007/BF03170785

Keywords

Search

Navigation