Sulfur-containing dihydro-pyrrolo [60]fullerene derivatives via 1,3-dipolar cycloadditions of glycine imine esters to C60

C₆₀ reacts thermally with 1,3-dipoles, formed in situ, from sulfide-bearing imines of glycine esters, and affords dihydro-pyrrolo [60]fullerene derivatives containing a vinylic sulfide group, which were isolated in good yields, and characterized with ¹H and ¹³C NMR, FTIR, UV-vis spectroscopies, and with FAB, ESI mass spectrometries. The new derivatives contain a sulfide, an imine, and an ester functionality for further chemical transformations. Mechanistic considerations with regard to the loss of a mercaptan molecule in the course of the cycloaddition are deployed.     

Reaction of a triazolinedione with simple alkenes. Isolation and characterization of hydration products

The reaction of N-phenyltriazolinedione with three simple alkyl-substituted alkenes in water/alcohol or water/acetone solution was found to give a mixture of the corresponding ene and water addition products. The new hydration products were characterized by spectroscopy, and in one case, also by X-ray diffraction analysis. Thermodynamic parameters were determined for the reactions involving 2-methylbut-2-ene, TriME, and 2,3-dimethylbut-2-ene, TetraMe, in accordance with an ‘S_N2-like’, nucleophilic attack on a closed aziridinium imide (AI) intermediate by water.     

Synthesis of PhTAD-substituted dihydropyrrole derivatives via stereospecific C–H amination

Research on Chemical Intermediates - Stereospecific α-amination has been accomplished via addition of N-phenyltriazolinedione (PhTAD) to the allylic position of dihydropyrroles. The aim of...     

N-Phenyltriazolinedione as an efficient, selective, and reusable reagent for the oxidation of thiols to disulfides

N-Phenyltriazolinedione is an efficient and chemoselective reagent for the oxidation of thiols to their corresponding symmetrical disulfides. The method is applicable to aromatic, aliphatic, and bi-functional thiols. The one-pot reaction takes a few minutes (in most cases studied) for completion and after a simple work-up affords the corresponding symmetrical disulfides in very good to excellent yields. Furthermore, the reaction could be performed with the same results in the absence of solvent for liquid thiols.