Refernces
10.1016/S0040-4020(97)00313-X
The research study on the efficient removal of sugar O-Tosyl groups and heterocyclic halogens from purine nucleosides using sodium naphthalenide. The purpose of this research was to develop an improved strategy for the synthesis of specific nucleosides by leveraging the high reduction potential of sodium naphthalenide, which is known for its ability to cleave carbon-halogen bonds and regenerate alcohols and amines from p-toluenesulfonate esters and p-toluenesulfonamides. The study concluded that sodium naphthalenide could effectively remove 2'-, 3'-, and 5'-O-tosyl groups from the sugar moiety of nucleosides, making p-toluenesulfonyl a viable protecting group. Additionally, it demonstrated the reductive cleavage of bromo or chloro groups from the 2-, 6-, or 8-position of purine nucleosides. Key chemicals used in the process included sodium naphthalenide, p-toluenesulfonate esters, p-toluenesulfonamides, and various purine nucleosides such as adenosine and its derivatives.
10.1039/c000695e
The research aimed to investigate the binding modes of phosphinine ligands on gold nanoparticles using solid-state 31P NMR spectroscopy. The study found that phosphinine ligands, which are used to stabilize gold nanoparticles during synthesis, react partially and form a mixture of intact phosphinine units and other surface-bound species. The intact phosphinines prefer h1(P)-coordination to a single gold atom, and the ligands are not mobile, as evidenced by the coupling with 197Au nuclei. The fraction of intact phosphinines decreases with less steric protection, but the product distribution does not simply correlate with substituent patterns. The key chemicals used in the research include phosphinine ligands (1, 2, and 3 with different substituent patterns), gold salts such as [(thp)AuCl] (thp = tetrahydrothiophene), and sodium naphthalenide for the reduction process. The findings suggest that the superior stabilization of nanoparticles by phosphinines without bulky a-substituents is due to tighter binding and higher yields of strongly donating phosphine-type products.
10.3987/COM-04-10142
The research investigates the effects of sodium naphthalenide, a single electron transfer (SET) reagent, on 3-substituted indoles to explore the synthesis of indole derivatives through SET reactions. The study found that indoles with electron-donating substituents do not react with sodium naphthalenide, while those with electron-withdrawing substituents readily undergo reactions, yielding various products depending on the specific substituent. For instance, 3-trifluoroacetylindole, 3-acetylindole, and 3-benzoylindole each produced a single product, whereas 3-formylindole generated four products. The reactions involving electron-withdrawing groups were highly selective and efficient, with high yields of the desired products. The study concludes that SET reactions with sodium naphthalenide are an effective method for constructing indole derivatives when electron-withdrawing substituents are present on the indole ring, as these groups lower the LUMO energy of the indole ring, facilitating electron transfer from the reagent to the substrate.