77643-41-5Relevant academic research and scientific papers
Composes sulfures heterocycliques. XC (1). Reactions du diethylamino-1 propyne sur divers sels de dithiole-1,2 ylium
Dibo, Ahamada,Stavaux, Madeleine,Lozac'H, Noel
, p. 539 - 544 (2007/10/02)
The nucleophilic properties of ynamines and the electrophilic character of 1,2-dithiolylium cations are well known and it seemed interesting to study how they react together.The reaction of 3-methylthio-1,2-dithiolium salts 1 with 1-diethylaminopropyne 2 is performed in acetonitrile.The resulting mixture is then treated by H2S or NaHS.Under action of H2S, a 6-methylthiothiopyran-2-thione 3 is obtained whereas an excess of NaHS leads to 3 accompained by a 6-diethylaminothiopyran-2-thione 4. .Structures of 3 and 4 have been deduced from elemental analysis, NMR, UV spectra and some chemical properties.For instance, under action of methyl iodide, a compound 3 led to a symmetrical product, a fact consistent with the proposed structure.Like 3-methylthio-1,2-dithiolium iodides, 1,2-dithiol-3-iminium iodides 5 react with 1-diethylaminopropyne.When the reaction mixture is treated by H2S, a 2-diethylamino-1,6,6aλ4-trithiapentalene 6 is obtained whereas an excess of NaHS leads both to 6 an to a 2-diethylaminothiopyran-4-thione 7. .One of the compounds 6 thus obtained is identical to a sample of 1,6,6aλ4-trithiapentalene prepared in another way and the structure of 7 has been deduced from elemental analysis, NMR and UV spectra.
