- 4-Dodecylbenzenesulfonic acid (DBSA) promoted solvent-free diversity-oriented synthesis of primary carbamates, S-thiocarbamates and ureas
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A simple and highly efficient solvent-free method for the conversion of alcohols, phenols, thiols and amines to primary carbamates, S-thiocarbamates and ureas in the presence of 4-dodecylbenzenesulfonic acid (DBSA) as a cheap and green Bronsted acid reagent has been described. All products were obtained in good to excellent yields and characterized using FT-IR, 1H- and 13C-NMR, MS and CHNS techniques.
- Sardarian, Ali Reza,Inaloo, Iman Dindarloo
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p. 76626 - 76641
(2015/09/22)
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- The E1cB Mechanism for Thiocarbamate Ester Hydrolysis: Equilibrium and Kinetic Studies
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The alkaline hydrolyses of a series of S-aryl thiocarbamate esters have been measured and the mechanism confirmed to be dissociative.Equilibrium constant for the synthesis of thiocarbamates from thiol and isocyanic acid have been obtained for aqueous media using both kinetic and analytical techniques.Hammett and Broensted parameters for the equilibrium reaction indicate that there is less positive effective charge on the sulphur in the thiocarbamate compared with that on the oxygen in the oxygen analogue.Theoretical arguments are advanced to show that the dissociative reactions of simple carbamate anions involve a planar geometry of the paticipating atoms.
- Bourne, Nicholas,Williams, Andrew,Douglas, Kenneth T.,Penkava, Thomas R.
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p. 1827 - 1832
(2007/10/02)
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