10.1016/S0040-4020(01)90619-2
The research investigates the reaction of cyclic thioacetals and thioketals (1,3-dithiolanes) with halogens in anhydrous carbon tetrachloride at room temperature. The study aims to develop a mild and convenient method for thioketal hydrolysis using halogens as inexpensive and readily available demasking reagents. The researchers found that the cleavage of 1,3-dithiolanes to carbonyl compounds occurs via monocationic intermediates rather than the previously proposed dicationic species. Various chemicals played significant roles in the research, including 1,3-dithiolanes, halogens such as iodine, bromine, and chlorine, anhydrous carbon tetrachloride as the solvent, and in some experiments, iodotrimethylsilane and dimethyl sulfoxide. The study also explored the effects of different substituents at the C-2 position of the dithiolane ring on the reaction mechanism and outcomes, revealing that the structure of the parent carbonyl compound greatly influences the reaction pathway.
10.1021/je60040a035
The study investigates the physical and spectral properties of a series of heterocyclic compounds, including 2-aryl-1,3-dioxolanes, 1,3-dithiolanes, 1,3-oxathiolanes, and 1,3-N,N-dimethyl imidazolidines. These compounds were synthesized using standard procedures, with aldehydes and glycols (or their heteroanalogues) as starting materials, and p-toluene sulfonic acid as a catalyst. The study focuses on characterizing these compounds through their densities, refractive indexes, melting and boiling points, and infrared (IR) and nuclear magnetic resonance (NMR) spectra. Key findings include the identification of characteristic IR bands between 10.0 and 11.1 microns (1000 to 901 cm?1) for the heterocyclic five-membered ring, which are useful for analysis in the presence of typical starting materials. The NMR spectra reveal distinct chemical shifts for the benzylic hydrogens of these heterocyclic systems, which are insensitive to substituents on the phenyl rings. The study aims to provide detailed spectral data for these compounds to support further kinetic investigations, such as autoxidations, hydrolyses, and hydrogen abstraction reactions.