Competitive eliminations in the basic decomposition of N-alkoxypyridinium salts. I. Competition between ylide or anhydro base intermediates and hydroxide ions in the abstraction of α or β protons in the alkoxyl chain was written by Sliwa, H.;Tartar, A.. And the article was included in Tetrahedron in 1977.Synthetic Route of C7H9NO This article mentions the following:
A novel mode of base-induced decomposition of N-alkoxypyridinium salts with a β-H in the alkoxy chain is described. The N-oxide moiety acts as a leaving group in an elimination reaction to give an ethylenic derivative, in competition with the classical decomposition to aldehyde and pyridine. The latter is predominant in I (R = H, R1 = R2 = Me; R = R1 = H, R2 = Me) whereas the former is almost exclusive in I (R = H, Me; R1 = R2 =H). Deuteration studies showed that proton abstraction results from direct attack by OH– except for the α-proton of salts bearing ≥1 Me group in the 2- or 6-positions, where it occurs by an intramol. transfer to an intermediary anhydro base. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Synthetic Route of C7H9NO).
3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Synthetic Route of C7H9NO