Thiocarbonyl compounds

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General structure of a thioarbonyl compound (thiocarbonyl group shown in blue ):
Thioketone: A, B = org. Remainder
thioaldehyde: A = H , B = org. Remainder
thionecarboxylic acid: A = OH, B = org.
Thionamide residue  : A = NH 2 , NHR, NR 1 R 2 , B = org. Residual
thione: A = OR, B = org. rest

Thiocarbonyl compounds are carbonyl compounds in which the oxygen atom of a carbonyl group has been replaced by a sulfur atom. Thioaldehydes are the sulfur analogues of aldehydes and thioketones are the sulfur analogues of ketones . Thionamides are the sulfur analogues of amides and also contain a thiocarbonyl group, as do organyl isothiocyanates (organyl mustard oils ), the sulfur analogues of organyl isocyanates .

synthesis

Carbonyl compounds are converted into thiocarbonyl compounds through reaction with sulfurizing reagents (thionation reagents). There are a greater number of thionating agents. Phosphorus- containing agents include phosphorus (V) sulfide (P 4 S 10 ), Lawesson's reagent , the pyridine -P 4 S 10 complex pentathiodiphosphoric acid- P , P ′ -bis (pyrididium betaine ) and thiophosphoryl trichloride (PSCl 3 ) . The addition of Grignard compounds to carbon disulfide gives dithiocarboxylic acid esters (thionthiol carboxylic acid esters).

See also

Individual evidence

  1. ↑ Alexander Schönberg , Annemarie Wagner: Methods for the production and conversion of thioaldehydes and thioketones. In: Eugen Müller (ed.): Methods of Organic Chemistry. with the participation of Otto Bayer , Hans Meerwein and Karl Ziegler . Volume IX: Sulfur, Selenium , Tellurium Compounds. Thieme-Verlag, Stuttgart 1955, DNB 457585633 , pp. 695-740.
  2. ↑ Otto-Albrecht Neumüller (Ed.): Römpps Chemie-Lexikon. Volume 1: A-Cl. 8th revised and expanded edition. Franckh'sche Verlagshandlung, Stuttgart 1979, ISBN 3-440-04511-0 , p. 141.
  3. ↑ J. Bergman, B. Pettersson, V. Hasimbegovic, PH Svensson: Thionations Using a P4S10-Pyridine Complex in Solvents such as Acetonitrile and Dimethyl Sulfone. In: J Org Chem. Volume 76, 2011, pp. 1546-1553, doi: 10.1021 / jo101865y .
  4. ↑ U. Pathak, LK Pandey, R. Tank: Expeditious Microwave-Assisted Thionation with the System PSCl3 / H2O / Et3N under Solvent-Free Condition. In: J Org Chem. Volume 73, 2008, pp. 2890-2893, doi: 10.1021 / jo7022069 .
  5. ^ Siegfried Hauptmann : Organic chemistry. 2nd, revised edition. VEB Deutscher Verlag für Grundstofftindustrie, Leipzig 1988, ISBN 3-342-00280-8 , p. 459.