35776-03-5Relevant academic research and scientific papers
UNSATURATED THIOLATES AND THEIR ANALOGS IN CYCLOADDITION REACTIONS XI. EFFECT OF SUBSTITUENTS AT THE β POSITION OF ETHENETHIOLATES ON THE DIRECTION OF REACTION WITH CARBON BISULFIDE
Bobylev, V. A.,Petrov, M. L.,Petrov, A. A.
, p. 239 - 245 (2007/10/02)
1-Dialkylamino-, 1-alkylarylamino-, and 1-cycloalkylaminoethenethiolates react with carbon bisulfide in various directions, depending on the nature of the substituents at the position 2.In all cases 1,2-dithiole-3-thiones are formed.Thiolates unsubstituted at position 2 give, in addition, 5,5'-bis(dialkylamino)-, 5,5'-bis(alkylarylamino)-, and 5,5'-bis(cycloalkylamine)-1,1',2,2'-tetrathiafulvalenes.In the case of potassium 1-morpholino-2-tert-butylethenethiolate the reaction is accompanied by the elimination of a molecule of morpholine and by the formation of 4-tert-butyl-1,2-dithiole-3-thione.In the presence of a weak proton donor (acetonitrile) ethylenethiolates substituted at position 2 react normally, but the 1-piperidinoethenethiolate gives mainly N,N-pentamethylenetrithiomalonamide.
UNSATURATED THIOLATES IN CYCLOADDITION REACTIONS. III. REACTION OF 1-N,O,S-SUBSTITUTED 2-ALKYL- AND 2-PHENYL-1-ETHENETHIOLATES WITH CARBON BISULFIDE
Bunina, N. A.,Petrov, M. L.,Petrov, A. A.
, p. 11 - 17 (2007/10/02)
The reaction of 1-N,O,S-substituted 1-ethenethiolates with carbon bisulfide leads to the formation of cyclic adducts.The reaction rate decreases in the order N > O > S.In the case of the 1-N- and 1-S-substituted 1-ethenethiolates the reaction products are 5-N- and 5-S-substituted 1,2-dithiole-3-thiones.In the case of the 1-O-substituted 1-ethenethiolates the reaction goes further with the formation of 3,3'-spirobi(1,2-dithiole).The relation reaction rate constants for 1-N,N-dimethylamino-2H-, 1-N,N-dimethylamino-2-methyl-, and 1-N,N-dimethylamino-2-phenyl-1-ethenethiolates are 1, 4.2 and 10 respectively.
