10292-98-5Relevant academic research and scientific papers
The Willgerodt-Kindler Reactions. 6. Isomerization of the Carbonyl Group in Alkanones and Cycloalkanones
Carmack, Marvin,Behforouz, Mohammad,Berchtold, Glenn A.,Berkowitz, Samuel M.,Wiesler, Donald,Barone, Ralph
, p. 1305 - 1318 (2007/10/02)
The most unusual feature of the Willgerodt-Kindler Reactions is the facile isomerization of the carbonyl function along a chain of unbranched methylene groups, or around a cycloaliphatic ring containing several connected methylene groups.We have demonstrated that the first step in the Kindler process is the formation of enamines by reaction of the carbonyl function with secondary aliphatic amines, followed by reaction of the enamine with certain sulfur-amine catalysts to form reactive heterocyclic sulfur intermediates that facilitate the elimination-readdition of the amines reversibly along the chain.It was shown that compounds of the type R2N-S-S-NR2 are effective catalysts but not compounds of the type R2N-S-NR2.Some cyclohexanone derivatives undergo aromatization, with anomalous results in certain cases.
MERCURATION OF BORNYLENE. EFFECT OF THE ELECTROPHILICITY OF THE REAGENT AND SOLVENT ON THE RATIO OF REACTION PRODUCTS
Skorobogatova, E. V.,Povelikina, L. N.,Kartashov, V. N.
, p. 1979 - 1982 (2007/10/02)
In the mercuration of bornylene a Wagner-Meerwein rearrangement takes place in addition to the path leading to the formation of exo-addition products.The ratio between the reaction products varies over a wide range, depending on nature of the reagent and the solvent.It is suggested that the structure of the intermediate acquires the character of an unsymmetrical β-mercury-containig ion with increase in the hardness of the electrophilic reagent.
