Studies on organophosphorus compounds XX. syntheses of thioketones
- 1 January 1978
- journal article
- research article
- Published by Wiley in Bulletin des Sociétés Chimiques Belges
- Vol. 87 (3) , 223-228
- https://doi.org/10.1002/bscb.19780870310
Abstract
Substituted benzophenones, 2‐benzoylthiophene, 3‐benzoylpyridine, dicyclopropyl ketone, and camphor are converted into the corresponding thioketones after reaction with the dimer of p‐methoxyphenylthionophosphine sulfide, 1. Except for the pyridine derivatives (2‐ and 4‐benzoylpyridines, respectively, gave no thioketones) very high yields are found. Under the same conditions dibenzylketone gave 1,3‐diphenylpropene‐2‐thiol and 1,9‐benzanthr‐10‐one yielded the dimer of 1,9‐benzanthr‐10‐thione. Aromatic thioketones are also obtained by reacting gem‐dichlorides with 2‐methyl‐2‐propane‐thiol in the presence of catalytic amounts of CF3COOH (or AlCl3). A mechanism is suggested based on kinetic measurements. 13C NMR data of the thiocarbonyls of all thioketones are recorded and a function describing the relation between the chemical shifts of CS and CO is found: δCS1.57 δCO=71.45Keywords
This publication has 17 references indexed in Scilit:
- Studies on Organophosphorus Compounds XIX. About PSClx (NMe2)3‐x Compounds as Thiation ReagentsBulletin des Sociétés Chimiques Belges, 1977
- Studies on Organophosphorus Compounds XVI On O,O‐Dialkyl Dithiophosphoric Acids and N, N, N′, N′‐Tetramethylthiophosphoric Diamide as Thiation Agents: Conversion of Carboxamides into Thiocarboxamides, Alkyl Dithiocarboxylates, or NitrilesBulletin des Sociétés Chimiques Belges, 1977
- Studies on Organophosphorus Compounds. XVII. About O,O-Diethyl Dithiophosphoric Acid as Thiation and Alkylation Agent. A New Route to Dithiocarboxylic Esters and (Ethylthio) Heterocycles.Acta Chemica Scandinavica, 1977
- A General Procedure for the Conversion of a Carbonyl Group into a Thione Group with Tetraphosphorus DecasulfideSynthesis, 1973
- Organische Schwefelverbindungen, LIII. Über die Überführung gem. Dichloride der Xanthen‐ und Chromen‐Reihe in Thioketone, sowie deren Umsetzung mit Diazoessigester zu β.β‐disubstituierten AcrylsäureesternEuropean Journal of Inorganic Chemistry, 1968
- Umsetzungen mit p-methoxyphenyl-dithio-phosphonsäure-anhydridTetrahedron Letters, 1967
- Chemische Reaktionen der PerthiophosphonsäureanhydrideZeitschrift für anorganische und allgemeine Chemie, 1967
- The Preparation of Thiones in the Presence of Anhydrous Hydrogen FluorideThe Journal of Organic Chemistry, 1964
- Über Thio‐benzophenonBerichte der deutschen chemischen Gesellschaft (A and B Series), 1928
- Darstellung aromatischer Thio‐ketone durch Einwirkung von Thio‐essigsäure auf Ketochloride. Über die Einwirkung von Kupfer‐Bronze auf Thio‐benzophenon und seine Derivate. (9. Mitteilung) über organische SchwefelverbindungenBerichte der deutschen chemischen Gesellschaft (A and B Series), 1928