Skip to main content
Log in

3-Nitro-5-chloromethylsalicylaldehyde in the synthesis of photochromic spirochromenes of the indoline series

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The nitration of 5-chloromethylsalicylaldehyde leads to 3-nitro-5-chloromethylsalicylaldehyde, the chlorine atom in which is smoothly replaced by a hydroxy or acetoxy group. The salicylaldehydes obtained condense with 1,3,3-trimethyl-2-methylene-indoline to give the corresponding photochromic indolinespirochromenes. The spectral-kinetics of the photochromic transformations of the spirochromenes are discussed.

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. L. D. Taylor, US Patent No. 3507921 (1970); Chem. Abstr.,73, 3819 (1970).

    Google Scholar 

  2. S. J. Angyal, P. S. Morris, J. R. Tetaz, and J. G. Wilson, J. Chem. Soc., 2141 (1950).

  3. K. Auwers and R. Bondy, Ber.,37, 3915 (1904).

    Google Scholar 

  4. V. I. Pantsyrnyi, M. A. Gal'bershtam, and N. A. Donskaya, Khim. Geterotsikl. Soedin., No. 5, 653 (1973).

    Google Scholar 

  5. M. A. Gal'bershtam, L. M. Mikheeva, and N. P. Samoilova, Khim. Geterotsikl. Soedin., No. 11, 1534 (1972).

    Google Scholar 

  6. M. A. Gal'bershtam, N. M. Przhiyalgovskaya, N. P. Samoilova, E. V. Braude, I. B. Lazarenko, and N. N. Suvorov, Khim. Geterotsikl. Soedin., No. 1, 79 (1977).

    Google Scholar 

  7. E. V. Braude and M. A. Gal'bershtam, Khim. Geterosikl. Soedin., No. 7, 943 (1974).

    Google Scholar 

  8. R. C. Bertelson, Photochromism (edited by G. Brown), Vol. 3, Wiley-Interscience (1971) p. 73.

  9. A. I. Kiprianov, Usp. Khim.,29, 1336 (1960).

    Google Scholar 

  10. V. I. Pantsyrnyi and M, A. Gal'bershtam, Khim. Geterotsikl. Soedin., No. 5, 659 (1973).

    Google Scholar 

  11. E. Berman, R. E. Fox, and F. D. Thomson, J. Am. Chem. Soc.,81, 5605 (1959).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 196–199, February, 1978.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Braude, E.V., Gal'bershtam, M.A. 3-Nitro-5-chloromethylsalicylaldehyde in the synthesis of photochromic spirochromenes of the indoline series. Chem Heterocycl Compd 14, 153–156 (1978). https://doi.org/10.1007/BF00945328

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00945328

Keywords

Navigation