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.
Similar content being viewed by others
Literatur
H. R. Schweizer, Helv. Chim. Acta52, 2221 (1969).
P. Hrnčiar, Chem. Zvesti, im Druck.
S. Gabriel undA. Neumann, Ber. dtsch. chem. Ges.26, 951 (1893).
S. A. Osedčij undB. A. Barchač, J. Org. Chim. [russ.]6, 1815 (1970).
O. Bromler, Ber. dtsch. chem. Ges.29, 1436 (1896).
G. J. Vanag, Ja. Jo. Drogerie undJa. Ja. Crol Izv. Akad. Nauk Latv. SSR Ser. Chim.1964, 480.
P. Hrnčiar, Acta Facult. Rer. Natur. Univ. Comen. IX, 527 (1969).
V. Oškaja undG. Ja. Vanag, Izv. Akad. Nauk Latv. SSR, Ser. Chim.1962, 87.
S. V. Vinogradova, V. V. Korschak undS. N. Salarkin, J. Prikl. Chim.44, 1389 (1971).
V. Oškaja undG. Ja. Vanag, Izv. Akad. Nauk Latv. SSR, Ser. Chim.1964, 271.
L. H. Jale, J. Amer. Chem. Soc.69, 1547 (1947).
A. Perjéssy undP. Hrnčiar, Tetrahedron27, 6159 (1971).
R. Ja. Gren undG. Ja. Vanag, Izv. Akad. Nauk Latv. SSR, Ser. Chim.1961, 217.
W. E. Hahn undB. Rybczynski, Acta Chim. Łodź Tow. Nauk III,15, 85 (1970); Chem. Abstr.75, 98509 u.
Author information
Authors and Affiliations
Rights 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
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00910036