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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.

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Metadaten
Author:Ali Reza Modarresi-Alam, Iman Dindarloo Inaloo, Erich Kleinpeter
DOI:https://doi.org/10.1016/j.molstruc.2012.05.033
ISSN:0022-2860 (print)
Parent Title (English):Journal of molecular structure
Publisher:Elsevier
Place of publication:Amsterdam
Document Type:Article
Language:English
Year of first Publication:2012
Year of Completion: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
Pagenumber:7
First Page:156
Last Page:162
Funder:Sistan & Baluchestan University Graduate Council
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert