117214-89-8Relevant articles and documents
HYDROCARBOXYLATION OF OLEFINS IN THE PRESENCE OF Pd(II) COMPLEXES
Karpyuk, A. D.,Petrov, E. S.,Beletskaya, I. P.
, p. 1028 - 1029 (1986)
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HYDROCARBOXYLATION OF 1-NONENE IN THE ACETONE-PdCl2(PPh3)2-PPh3 SYSTEM AT LOW CO PRESSURE
Karpyuk, A.D.,Kolosova, N.D.,Terekhova, M.I.,Chernoplekova, V.A.,Petrov, E.S.,Beletskaya, I.P.
, p. 2091 - 2094 (1984)
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Mild, single-pot hydrocarboxylation of linear C5-C9 alkanes into branched monocarboxylic C6-C10 acids in copper-catalyzed aqueous systems
Kirillova, Marina V.,Kirillov, Alexander M.,Pombeiro, Armando J.L.
experimental part, p. 106 - 113 (2012/04/04)
A single-pot method has been developed for the hydrocarboxylation of the liquid C5-C9 alkanes (n-pentane, n-hexane, n-heptane, n-octane, n-nonane and 3-methylhexane) into the branched monocarboxylic C 6-C10 acids bearing one more carbon atom. This method is characterized by a direct, selective and low-temperature (60 °C) hydrocarboxylation reaction of the alkane with carbon monoxide, water (which acts as a reagent besides being a solvent component) and potassium peroxodisulfate, in H2O/MeCN medium. The hydrocarboxylations are markedly enhanced in the presence of a tetracopper(II) triethanolaminate complex as a homogeneous catalyst precursor. Total yields (based on alkane) of carboxylic acids up to 46% (with 97-99% overall selectivity) have been achieved, which are remarkable in the field of alkane functionalization under mild conditions, especially for a C-C bond formation reaction in aqueous acid-solvent-free medium. The regio- and bond selectivity parameters have been determined and a free radical mechanism has been proposed.
Syntheses of female sex pheromone precursors of pine sawfly species and of some structurally related methyl-branched long-chain 2-alkanols.
Hedenstroem, Erik,Andersson, Fredrik
, p. 1237 - 1254 (2007/10/03)
3,7-Dimethyl-2-undecanol, 3,7,9-trimethyl-2-tridecanol, and 3,7, 11-trimethyl-2-tridecanol were synthesized as racemic mixtures in moderate yields. The alcohols are known precursors of the female sex pheromones of the pine sawfly species Diprion nipponica, Macrodiprion nemoralis, and Microdiprion pallipes, respectively. Stereoisomeric mixtures of 3,8,12-trimethyl-2-tridecanol, erythro-(2R,3R, 11R/S)-3,11-dimethyl-2-tetradecanol, 3,5-dimethyl-2-tetradecanol, and 5,7-dimethyl-2-tetradecanol, structurally related to sex pheromone alcohol precursors of pine sawfly species, were also synthesized in moderate yields. The key reaction in the syntheses was the ring opening of gamma-butyrolactones by using different alkyl lithiums as nucleophiles.