lithium-perchlorate and nitromethane

We have developed a highly efficient synthetic method for azanucleosides using a lithium perchlorate-nitromethane reaction medium, allowing direct and exclusive installation of various nucleophiles, including protected nucleobases into prolinol derivatives at the preferred 5-position.

Topics: Aza Compounds; Electrochemical Techniques; Lithium Compounds; Methane; Nitroparaffins; Nucleosides; Perchlorates; Pyrrolidines

A new application of lithium perchlorate-nitromethane (LPNM) for the formation of aromatic C-N and C-C bonds is introduced. LPNM-promoted reactions of anilines with diarylmethanols selectively generate N-alkylated anilines or mono and double Friedel-Crafts alkylation products under different conditions by changing the reaction time, reaction temperature, and the ratio of the reactants. This method does not require the use of transition metal catalysts to prepare alkylated aniline derivatives.

Topics: Alkylation; Aniline Compounds; Lithium Compounds; Methane; Methanol; Nitroparaffins; Perchlorates

Topics: Alkenes; Electrochemistry; Electrolytes; Ethers; Lithium Compounds; Methane; Molecular Structure; Nitroparaffins; Perchlorates; Solutions; Stereoisomerism

[reaction: see text] N-Acyliminium cation of prolines was efficiently generated to accumulate in an undivided cell at 0 degrees C by an anodic oxidation of N-acylprolines or alpha'-phenylsulfanylated N-acylproline derivatives in a lithium perchlorate/nitromethane solution. The iminium cation intermediates gave modified prolines by a reaction with nucleophiles under mild conditions.

Topics: Electrodes; Electrolytes; Lithium Compounds; Methane; Nitroparaffins; Perchlorates; Proline; Solutions