- Mild, single-pot hydrocarboxylation of linear C5-C9 alkanes into branched monocarboxylic C6-C10 acids in copper-catalyzed aqueous systems
-
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.
- Kirillova, Marina V.,Kirillov, Alexander M.,Pombeiro, Armando J.L.
-
experimental part
p. 106 - 113
(2012/04/04)
-
- Determination of the relative and absolute configuration of the dimethylmyristoyl side chain of pneumocandin B0 by asymmetric synthesis
-
(Equation presented) The relative and absolute configuration of the pneumocandin B0 side chain has been established as (10R,12S)-dimethylmyristoyl by the stereocontrolled synthesis of both antipodes of the side chain acid and their comparison to a sample derived from the natural product.
- Leonard Jr., William R.,Belyk, Kevin M.,Bender, Dean R.,Conlon, David A.,Hughes, David L.,Reider, Paul J.
-
p. 4201 - 4204
(2007/10/03)
-
- Pheromones, 65. - Identification of the Volatile Components of the Mandibular Gland Secretion of the Ant Manica rubida: Structure Elucidation, Synthesis, and Absolute Configuration of Manicone
-
By means of gas chromatography and mass spectrometry, manicone, (4E)-4,6-dimethyl-4-octen-3-one (1), was identified as the main component of the mandibular gland secretion of the ant Manica rubida.In addition the presence of homomanicone (2), bishomomanicone (3), normanicone (7), and a few aliphatic aldehydes and ketones was also evident in the gland.Racemic 1, 2, and 7 and optically active dihydromanicone (4), were synthesized.The (S) configuration of 1 was determined by complexation gas chromatography, on a chiral phase, of 4 as well as of the hydrogenation products of racemic and natural 1.
- Bestmann, Hans Juergen,Attygalle, Athula B.,Glasbrenner, Juergen,Riemer, Roland,Vostrowsky, Otto,et al.
-
-