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Studies on organophosphorus compounds XX. syntheses of thioketones
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 CF 3 COOH (or AlCl3). A mechanism is suggested based on kinetic measurements. 13 C 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: δ CS1.57 δ CO=71.45
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Cited by
Thionation reactions of lawesson's reagents
Cava, M. P., & Levinson, M. I. (1985) · Tetrahedron · doi:10.1016/s0040-4020(01)96753-5 · Cited by 667
Thiopeptide Synthesis. α-Amino Thionoacid Derivatives of Nitrobenzotriazole as Thioacylating Agents
Shalaby, M. A., Grote, C. W., & Rapoport, H. (1996) · The Journal of Organic Chemistry · doi:10.1021/jo961245q · Cited by 133
Metadata
- Authors
- Pedersen, B. S., Scheibye, S., Nilsson, N. H., & Lawesson, S. ‐.
- Venue
- Bulletin des Sociétés Chimiques Belges
- Publisher
- Wiley
- Published
- 1978-01
- Volume
- 87
- Issue
- 3
- Pages
- 223-228
- ISSN
- 0037-9646 (ISSN-L)
- OpenAlex
- W2052665507
- Cited by
- 432
- References
- 0
- FWCI
- 11.16
- Type
- journal article
- Language
- en
- Open access
- closed
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- Pedersen, B. S., Scheibye, S., Nilsson, N. H., & Lawesson, S. ‐. (1978). Studies on organophosphorus compounds XX. syntheses of thioketones. Bulletin des Sociétés Chimiques Belges. https://doi.org/10.1002/bscb.19780870310
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