Refernces
10.1016/S0040-4039(00)01211-9
The research focuses on the novel synthesis of highly fluorescent hexaaryl[3]radialenes, which are compounds of interest due to their electron-rich nature and potential use in electron donor and acceptor systems. The synthesis involves the oligomerization of ate-type copper carbenoids, followed by cyclization with hexamethylditin and Pd(PPh3)4. The structures of the intermediate [3]dendralene and the final hexaaryl[3]radialenes were confirmed through X-ray crystallographic analysis. The experiments utilized reactants such as ate-type copper carbenoids, hexamethylditin, and Pd(PPh3)4, and employed various analytical techniques including NMR, UV spectroscopy, and cyclic voltammetry to characterize the compounds and measure their redox properties. The study also examined the fluorescence properties of the synthesized radialenes, finding that the introduction of a chlorine atom in compound 4 enhanced its fluorescence quantum yield compared to compound 3.
10.1021/jo00013a049
The research aims to develop a practical and general approach to synthesizing a series of β-(trialkylstannyl)vinyl sulfoxides and sulfones, which are important synthetic intermediates. The study explores alternative methods due to unsatisfactory yields from a literature procedure involving monolithiation and sulfenylation. The researchers discovered an efficient route by reacting sulfenyl chlorides with acetylene, followed by oxidation to obtain sulfoxides and sulfones. They then introduced the trialkylstannyl moiety using hexamethylditin and a palladium catalyst in N-methylpyrrolidinone (NMP), achieving good yields. The conclusions highlight the development of a high-yielding and scalable method for synthesizing these olefinic stannanes, which can be further utilized in Stille couplings to produce functionalized dienes.
10.1021/ja00247a049
The study focuses on the synthesis and characterization of tetramethyltetratellurafulvalene (TMTTeF) and its electrochemical properties. TMTTeF was synthesized using a method involving acetylene, hexamethylditin, n-BuLi, and elemental tellurium, with tetrachloroethylene as a reactant in the final step. The compound was purified through chromatography and characterized by spectroscopic methods, including mass spectrometry and NMR spectroscopy. The electrochemical data, obtained by cyclic voltammetry, revealed that TTeF exhibits two reversible one-electron oxidations, with an ionization potential between that of tetrathiafulvalene (TTF) and tetraselenafulvalene (TSF). The study also discusses the presence of a six-membered ring isomer in the crude TTeF, identified through an irreversible oxidation peak in the cyclic voltammogram. The research aims to explore the potential of TTeF in forming organic metals and to make this synthesis available to the broader scientific community for further exploration of its solid-state properties.
10.1039/b712856h
The research focuses on the diastereoselective synthesis of cyclic hydrazines through a carbocyclisation process involving allene-hydrazones. The purpose of this study was to develop a synthetic method that could construct complicated molecules from simpler starting materials using transition metal-catalyzed reactions. The researchers discovered that by introducing a hydrazone functionality, they could convert allene-imine to cyclic products with good yield and excellent diastereoselectivity. The key chemicals used in this process include allene-hydrazones, palladium catalysts for distannylation, titanium tetrachloride (TiCl4) as a Lewis acid for the intramolecular allylic transfer, and stannanes like Me3SnSnMe3. The conclusions of the study highlight the synthetic utility of this method, which involves the distannylation of an allene by a palladium catalyst, transmetallation of the allylstannyl moiety to a titanium species, and the subsequent intramolecular allylic transfer reaction with the hydrazone.
