2050-77-3Relevant articles and documents
The fluid-mosaic model, homeoviscous adaptation, and ionic liquids: Dramatic lowering of the melting point by side-chain unsaturation
Murray, Samuel M.,O'Brien, Richard A.,Mattson, Kaila M.,Ceccarelli, Christopher,Sykora, Richard E.,West, Kevin N.,Davis Jr., James H.
, p. 2755 - 2758 (2010)
(Figure Presented) Defying conventional wisdom: Ionic liquids (ILs) with long, unsaturated alkyl appendages (see top structure) defy established trends that link long ion-bound alkyl groups to higher melting points. The new ILs are also less viscous than a saturated standard (see bottom structure) at the same temperature. These features parallel those that underpin homeoviscous adaptation in certain organisms and are indirectly supportive of a fluid-mosaiclike nanoscale character.
Catalytic Iodination of the Aliphatic C-F Bond by YbI3(THF)3: Mechanistic Insight and Synthetic Utility
Janjetovic, Mario,Ekebergh, Andreas,Tr?ff, Annika M.,Hilmersson, G?ran
supporting information, p. 2804 - 2807 (2016/07/06)
A facile iodination protocol of unactivated alkyl fluorides using catalytic amounts of YbI3(THF)3 in the presence of iodotrimethylsilane as a stoichiometric fluoride trapping agent is presented. 1H NMR spectroscopy demonstrates a two-step catalytic cycle where TMSI regenerates active YbI3(THF)3. Finally, the catalytic reaction is extended into a one-pot procedure to demonstrate a potential application of the method. Overall, the findings present a distinct strategy for C-F bond transformations in the presence of catalytic YbI3(THF)3.
Asymmetric total synthesis of all four isomers of 6-acetoxy-5- hexadecanolide: The major component of mosquito oviposition attractant pheromones
Dong, Hong-Bo,Yang, Ming-Yan,Zhang, Xiao-Teng,Wang, Ming-An
, p. 610 - 616 (2014/05/20)
An asymmetric total synthesis of (5S,6R)-(+)-erythro-6-acetoxy-5- hexadecanolide 1a has been accomplished from readily available hex-5-yn-1-ol via Shi's asymmetric epoxidation as the key step, in eight steps with an overall yield of 33.5%. In addition, the stereoselective synthesis of all four isomers of 6-acetoxy-5-hexadecanolide 1a-1d were obtained via Sharpless asymmetric dihydroxylation and Mitsunobu reaction as the key steps with overall yields of 16.5-21.2%, respectively.