Synthesis of primary thiocarbamates by silica sulfuric acid as effective reagent under solid-state and solution conditions
- A simple and efficient method for the conversion of alcohols and phenols to primary O-thiocarbamates and S-thiocarbamates in the absence of solvent (solvent-free condition) using silica sulfuric acid (equivalent to SiO2-OSO3H) as a solid acid is described. The products are easily distinguished by IR, NMR and X-ray data. X-ray data of the compounds reveal a planar trigonal orientation of the NH2 nitrogen atom with the partial C,N double-bond character and the C=S or C=O groups in synperiplanar position with C-aryl-O and C-alkyl-S moieties, respectively. Moreover, the -O-CS-NH2 group which is perpendicular to the plane of the benzene ring in 1c and the central thiocarbamate -S-CO-NH2 group in 2b are essentially planar.
| Author details: | Ali Reza Modarresi-Alam, Iman Dindarloo Inaloo, Erich KleinpeterORCiDGND |
|---|---|
| DOI: | https://doi.org/10.1016/j.molstruc.2012.05.033 |
| ISSN: | 0022-2860 |
| Title of parent work (English): | Journal of molecular structure |
| Publisher: | Elsevier |
| Place of publishing: | Amsterdam |
| Publication type: | Article |
| Language: | English |
| Year of first publication: | 2012 |
| Publication year: | 2012 |
| Release date: | 2017/03/26 |
| Tag: | Isothiocyanic acid; N-unsubstituted (primary)S-thiocarbamates; N-unsubstituted(primary)O-thiocarbamates; Silica sulfuric acid; Solid acid; Solvent-free |
| Volume: | 1024 |
| Issue: | 9 |
| Number of pages: | 7 |
| First page: | 156 |
| Last Page: | 162 |
| Funding institution: | Sistan & Baluchestan University Graduate Council |
| Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
| Peer review: | Referiert |
