Synthesis and mass spectrometric study of condensed thiones: Precursors of thiophene heterofulvalenes

Autor: Litvinov, V. P., Dzhumaev, I. A., Zolotarev, B. M.
Zdroj: Russian Chemical Bulletin; September 1983, Vol. 32 Issue: 9 p1901-1906, 6p
Abstrakt: 1.Thieno(2,3-d)-1,3-dithiol-2-thione, thieno(2,3-d)-1,3-thioselenol-2-thione, and thieno(2,3-d)-1,3-diselenol-2-thione were prepared by successive treatment of 3-bromothiophene at -70°C with an ether solution of n-butyllithium, sulfur, or selenium, a second equivalent of n-butyllithium, sulfur or selenium, and an ether solution of thiophosgene at -20°C (without separation of intermediate products).2.Thieno(3,4-d)-1,3-dithiol-2-thione, thieno(3,4-d)-1,3-thioselenol-2-thione, and thieno(3,4-d)-1,3-diselenol-2-thione were prepared by dealkylation of 3,4-bis(ethylmercapto)-,3-ethylseleno-4-ethylmercapto-, and 3,4-bis(methylseleno)thiones with sodium in liquid ammonia and subsequent treatment of the disodium salts formed with thiophosgene in ether.3.The mass spectra of the thiones synthesized were studied and showed that a C4H2S+. ion (m/z 82), which could correspond to the structure of dehydrothiophene, was formed on decomposition of the molecular ions in all cases.
Databáze: Supplemental Index