Thione-thiol rearrangement of xanthates catalyzed by pyridine N-oxides. Remarkable enhanced reactivity of 4-dialkylaminopyridine N-oxides was written by Harano, Kazunobu;Nakagawa, Hidetoshi;Kamei, Kumiko;Kiyonaga, Hideo;Hisano, Takuzo. And the article was included in Chemical & Pharmaceutical Bulletin in 1992.Category: pyridine-derivatives This article mentions the following:
Pyridine N-oxides (III; R = electron-donating substituents) are efficient catalysts for rearrangement of O-alkyl S-Me dithiocarbonates (xanthates) (I) to the corresponding S-alkyl S-Me dithiocarbonates (dithiolcarbonates) (II). Of the catalysts tested, III [R = piperidino (IV)] is the best from the viewpoints of catalytic activity and solubility in I. Heating of I in the presence of catalytic amounts (0.02-0.05 M eq) of IV gave II together with the sym. S,S-dialkyl and S,S-di-Me dithiocarbonates in good yields. The catalytic behavior of III is discussed on the basis of kinetic and MO data. The complete calculation of the perturbation equation on the initial stage of the reaction was consistent with the exptl. observed activity of the catalysts. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Category: pyridine-derivatives).
3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Category: pyridine-derivatives