127911-15-3Relevant articles and documents
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 (1997)
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.
High-Throughput Synthesis of (S)-α-Phellandrene through Three-Step Sequential Continuous-Flow Reactions
Miller, Samuel J.,Ishitani, Haruro,Furiya, Yuichi,Kobayashi, Shū
supporting information, p. 192 - 198 (2021/02/05)
The combination of continuous-flow processing with heterogeneous catalysts allows for efficient, sustainable, multistep synthesis. Here, we report the continuous-flow synthesis of a valuable terpene product, phellandrene, from a readily available natural feedstock. The protocol consists of selective hydrogenation using a highly active and stable supported platinum catalyst, dehydrative hydrazone formation, followed by the Shapiro reaction. Appropriate design of the reactor allowed for high productivity and space-time yield. Phellandrene was synthesized on a 30-g scale over 6 h, giving high yields, purity, and productivity.
Cyclic Ether Synthesis via Palladium-Catalyzed Directed Dehydrogenative Annulation at Unactivated Terminal Positions
Thompson, Samuel J.,Thach, Danny Q.,Dong, Guangbin
supporting information, p. 11586 - 11589 (2015/09/28)
Here, a palladium-catalyzed functionalization of unactivated sp3 C-H bonds with internal alcohol nucleophiles is described. Directed by an oxime-masked alcohol, annulation chemoselectively occurs at the β position, leading to a range of aliphatic cyclic ethers with four- to seven-membered rings. Tethered primary, secondary, and tertiary free hydroxyl groups can all react to give the corresponding cyclized products. In addition, benzyl and silyl protected alcohols can also be directly coupled. An sp3 C-H activation/intramolecular SN2 pathway was proposed.
Regioselective mono-deprotection of di-ferf-butylsilylene acetal derived from 1,3-diol with ammonium fluoride
Ohtawa, Masaki,Tomoda, Hiroshi,Nagamitsu, Tohru
supporting information, p. 113 - 118 (2014/02/14)
Here we report a novel and efficient method for the regioselective mono-deprotection of di-terf-butylsilylene acetals derived from 1,3-diols consisting of primary and secondary alcohols. The ammonium fluoride-mediated reactions of pyripyropene A derivative, thymidine and uridine derivatives, methyl β-D-glucofuranoside, and pyranoside derivatives each gave the corresponding primary alcohol with high regioselectivity.