Showing papers by "Yu. N. Ogibin published in 1976"
TL;DR: In this article, a new method was proposed for the synthesis of γ-alkyl-Δα,β-butenolides by oxidative dehydrocarboxylation ofγ -alkylparaconic acids by the S2O82−-AgNO3-CuSO4 system.
Abstract: A new method is proposed for the synthesis of γ-alkyl-Δα,β-butenolides by oxidative dehydrocarboxylation ofγ -alkylparaconic acids by the S2O8
2−-AgNO3-CuSO4 system.
1 citations
TL;DR: In this article, the relationship between the ability of these radicals to undergo oxidative cyclization to lactones and the number of methylene groups (n) and also the effect of copper ions on the oxidative cyclization process was investigated.
Abstract: 1.
ω-Carboxyalkyl radicals HOOC(CH2)nCH2, where n=4–7, were generated by the oxidative decarboxylation of pentane-, hexane-, heptane-, and octanedicarboxylic acids at 60°C in aqueous solution by the action of Na2S2O8 in the presence of silver nitrate. The relation between the ability of these radicals to undergo oxidative cyclization to lactones and the number of methylene groups (n) and also the effect of copper ions on the oxidative cyclization process were investigated.
2.
The main products from oxidative cyclization ofω-carboxyalkyl radicals in the absence of copper ions areγ-alkyl-γ-butyrolactones. In addition, alkanoic acids (84–95%) are formed as a result of abstraction of H atoms from the organic substrates by the radicals.
3.
The main products from the oxidative cyclization of theω-carboxyalkyl radicals in the presence of copper ions areγ-alkyl-Δα,β-butenoiides.ω-Alkenoic acids (58–98%) are formed as a result of the oxidativeβ-deprotonation of the radicals by the action of Cu(II).