Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Darstellung und einige Spektraleigenschaften des 5,6-Dihydro-4,7-dithiaindan-1,3-dions

Preparation and some spectral properties of 5.6-dihydro-4.7-dithiaindan-1.3-dione

  • 19 Accesses

  • 2 Citations

Abstract

The preparation of 5.6-dihydro-4.7-dithiaindan-1.3-dione (I) and its 2-methyl and 2-ethyl derivatives* is described, starting from 5.6-dihydro-pyrazine-2.3-dicarboxylic anhydride. The reaction of this anhydride with acetic anhydride, according theGabriel modification of thePerkin synthesis, resulted in 7-oxo-2.3.5.7-tetrahydrofuro[3.4-b]pyrazin-5-ylideneacetic acid while reaction with propionic acid anhydride and butyric acid anhydride resulted in 2-methyl (2-ethyl)-5.6-dihydro-4.7-dithiaindan-1.3-dione.

The1H-NMR and electronic spectra of I were measured in solvents with different dielectric constant and it was found that I is more stable in the diketo form than 1.3-indandione.

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

Literatur

  1. 1

    H. R. Schweizer, Helv. Chim. Acta52, 2221 (1969).

  2. 2

    P. Hrnčiar, Chem. Zvesti, im Druck.

  3. 3

    S. Gabriel undA. Neumann, Ber. dtsch. chem. Ges.26, 951 (1893).

  4. 4

    S. A. Osedčij undB. A. Barchač, J. Org. Chim. [russ.]6, 1815 (1970).

  5. 5

    O. Bromler, Ber. dtsch. chem. Ges.29, 1436 (1896).

  6. 6

    G. J. Vanag, Ja. Jo. Drogerie undJa. Ja. Crol Izv. Akad. Nauk Latv. SSR Ser. Chim.1964, 480.

  7. 7

    P. Hrnčiar, Acta Facult. Rer. Natur. Univ. Comen. IX, 527 (1969).

  8. 8

    V. Oškaja undG. Ja. Vanag, Izv. Akad. Nauk Latv. SSR, Ser. Chim.1962, 87.

  9. 9

    S. V. Vinogradova, V. V. Korschak undS. N. Salarkin, J. Prikl. Chim.44, 1389 (1971).

  10. 10

    V. Oškaja undG. Ja. Vanag, Izv. Akad. Nauk Latv. SSR, Ser. Chim.1964, 271.

  11. 11

    L. H. Jale, J. Amer. Chem. Soc.69, 1547 (1947).

  12. 12

    A. Perjéssy undP. Hrnčiar, Tetrahedron27, 6159 (1971).

  13. 13

    R. Ja. Gren undG. Ja. Vanag, Izv. Akad. Nauk Latv. SSR, Ser. Chim.1961, 217.

  14. 14

    W. E. Hahn undB. Rybczynski, Acta Chim. Łodź Tow. Nauk III,15, 85 (1970); Chem. Abstr.75, 98509 u.

Download references

Author information

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Hrnčiar, P., Sokolová, R. Darstellung und einige Spektraleigenschaften des 5,6-Dihydro-4,7-dithiaindan-1,3-dions. Monatshefte für Chemie 104, 1224–1230 (1973). https://doi.org/10.1007/BF00910036

Download citation