499-69-4Relevant 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.
Oxidoreduction between Cycloalkanols and Cycloalkanones in the Cultured Cells of Nicotiana tabacum. Simulation of the Time-courses in the Oxidation of (+)-Borneol and the Reduction of (-)-Carvomenthone
Suga, Takayuki,Izumi, Shunsuke,Hirata, Toshifumi,Hamada, Hiroki
, p. 425 - 428 (2007/10/02)
The time-courses in the oxidation of (+)-borneol and the reduction of (-)-carvomenthone in the cultured cells of Nicotiana tabacum were simulated on the basis of the permeability of 5- to 7-membered cycloalkanols and their corresponding cycloalkanones into the cultured cells and the 13C NMR chemical shifts of the carbonyl carbon of (+)-camphor which is the oxidation product of (+)-borneol and (-)-carvomenthone which is a substrate for the reduction, respectively.
