3858-47-7Relevant articles and documents
Simple H2-free hydrogenation of unsaturated monoterpenoids catalyzed by Raney nickel
Philippov, Alexey A.,Chibiryaev, Andrey M.,Martyanov, Oleg N.
, p. 380 - 381 (2019/08/20)
A series of monoterpenoids (citral, carvone, menthone, camphor) as well as cyclohexanone and hex-5-en-2-one were subjected to transfer hydrogenation with PriOH/Raney nickel system at 82 or 150 °C. Among monoterpenoids, citral and carvone underwent full conversion at 82 °C within 5 h.
Radical chain reduction of alkylboron compounds with catechols
Villa, Giorgio,Povie, Guillaume,Renaud, Philippe
supporting information; experimental part, p. 5913 - 5920 (2011/06/16)
The conversion of alkylboranes to the corresponding alkanes is classically per-formed via protonolysis of alkylboranes. This simple reaction requires the use of severe reaction conditions, that is, treatment with a carboxylic acid at high temperature (>150 °C). We report here a mild radical procedure for the transformation of organoboranes to alkanes. 4-tert-Butylcatechol, a well-established radical inhibitor and antioxidant, is acting as a source of hydrogen atoms. An efficient chain reaction is observed due to the exceptional reactivity of phenoxyl radicals toward alkylboranes. The reaction has been applied to a wide range of organoboron derivatives such as B- alkylcatecholboranes, trialkylboranes, pinacolboronates, and alkylboronic acids. Furthermore, the so far elusive rate constants for the hydrogen transfer between secondary alkyl radical and catechol derivatives have been experimentally determined. Interestingly, they are less than 1 order of magnitude slower than that of tin hydride at 80 °C, making catechols particularly attractive for a wide range of transformations involving C-C bond formation.
Influence of a non-micelle-forming surfactant on the electrocatalytic hydrogenation of carvone and limonene in aqueous medium at Raney nickel electrodes
Beraud,Lessard,Thomalla
, p. 1529 - 1535 (2007/10/03)
The electrocatalytic hydrogenation (ECH) of carvone (1) and limonene (8) at a Raney nickel cathode was studied in aqueous solutions containing a non-micelle-forming surfactant (didodecyldimethylammonium bromide, DDAB). The efficiency of ECH of these substrates was markedly increased compared to that observed previously with micelle-forming surfactants, and this for very low DDAB concentrations, as a consequence of strong adsorption of DDAB on the electrode. For the ECH of 8 in basic medium (pH 10), the major part of organic compounds (60-95%) was shown to be adsorbed on the electrode surface as an organic layer stabilized by an interfacial film of DDAB.
