95308-87-5Relevant academic research and scientific papers
Efficient Synthesis of Unsymmetrical Sulfamides via a Lossen-Like Rearrangement
Pantaine, Lo?c,Richard, Fran?ois,Marrot, Jér?me,Moreau, Xavier,Coeffard, Vincent,Greck, Christine
supporting information, p. 2012 - 2016 (2016/07/06)
A convenient one-pot synthesis of unsymmetrical sulfamides via a Lossen-like rearrangement is reported. The protocol operates under simple conditions at room temperature and does not require an inert atmosphere and a dry solvent. The ability of N-hydroxy arenesulfonamide O-derivatives to generate under mild conditions N-sulfonylimine intermediates was a trigger point for developing a general synthetic strategy towards unsymmetrical sulfamides. The synthetic potential of the methodology has been investigated by preparing cyclic sulfamides and new potential chiral organocatalysts. (Figure presented.) .
Basicity of Nitrogen-Sulphur(VI) Compounds. Part 6. Ionization of NN'-Di- and N-Mono-substituted Sulphamides and Dihydro-2,1,3-benzothiadiazoline and Benzothiadiazine 2,2-Dioxides (Cyclic Sulphamides)
Burke, Padraig O.,McDermott, Sean D.,Hannigan, Thomas J.,Spillane, William J.
, p. 1851 - 1854 (2007/10/02)
36 Di- and mono- and two tri-substituted sulphamides have been synthesised and their ionization equilibria in base (Schemes 1-3) have been studied.Many of the sulphamides are new materials.The pKa values obtained for each series have been correlated in Hammett and Taft plots.The Hammett ? values obtained for the ionization of the proximate hydrogen are ca. 2.3.The Taft ?* value obtained for ionization of the 'remoter' hydrogen is 1.68.The six-membered cyclic sulphamides are more acidic than their acyclic analogues by ca. 2.5 pKa units and the five-membered cyclic sulphamides are ca. 4 pKa units more acidic than model open-chain counterparts.Sulphur d-orbital involvement and ring-strain are suggested as possible sources of this 'acid-strengthening' effect.
