Spitzner, R. published the artcileKetovinylization of thiocarbamides and thioureas. On the ambidence of the thioamido function, HPLC of Formula: 6972-05-0, the publication is Tetrahedron (1982), 38(7), 927-36, database is CAplus.
Thiocarbamides and thioureas reacted as ambident systems with ¦Â-chlorovinyl ketones to give (S)-[(Z)-ketovinyl] salts. E.g., addition reaction of PhCSNH2 with PhCOCH:CHCl in HCO2H/HClO4 for 1-2 h gave 78% (Z)-PhCOCH:CHSCPh:N+H2 ClO4–. The ketovinyl salts obtained from monoprotic thiocarbamides and thioureas underwent deprotonation to give (S)-[(Z)-ketovinyl]thioimidate esters or -isothioureas, which isomerized intramolecularly on heating. E.g., deprotonation of (Z)-4-MeOC6H4COCH:CHSCPh:N+HPh ClO4– gave 82% (Z)-4-MeOC6H4COCH:CHSCPh:NPh, which on heating in PhMe gave (E)-4-MeOC6H4COCH:CHSCPh:NPh. Lithiated monoprotic thiocarbonamides reacted with ¦Â-chlorovinyl ketones to give N-[(E)-ketovinyl]thiocarbonamides, whereas lithiated thioureas gave S-[(E)-ketovinyl]isothioureas, which rearranged to the N-[(E)-ketovinyl]thioureas under mild conditions. E.g., lithiation and addition reaction of PhCSNHPh with PhCOCH:CHCl gave 59% (E)-PhCOCH:CHNPhCSPh, whereas similar treatment of Me2NC(S)NHPh gave (E)-PhCOCH:CHSC(:NPh)NMe2, which above room temperature gave (E)-PhCOCH:CHNPhC(S)NMe2.
Tetrahedron published new progress about 6972-05-0. 6972-05-0 belongs to catalysis-chemistry, auxiliary class Thiourea,Amine,Aliphatic hydrocarbon chain,Amide, name is 1,1-Dimethylthiourea, and the molecular formula is C8H5F3N4, HPLC of Formula: 6972-05-0.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia