58772-83-1Relevant academic research and scientific papers
Hydroformylation of myrcene: Metal and ligand effects in the hydroformylation of conjugated dienes
Foca, Claudia M.,Barros, Humberto J. V.,Dos Santos, Eduardo N.,Gusevskaya, Elena V.,Bayon, J. Carles
, p. 533 - 539 (2003)
The hydroformylation of myrcene catalyzed by Rh and Pt/Sn catalysts containing different P-donor ligands leads to the formation of a number of mono- and dialdehydes. Nine major products of the reaction have been characterized, showing that they arise from the n-alkyl and η3-allyl intermediates, formed through the reaction of the metal catalysts with the less substituted C=C bond of the substrate. Thus, 4-methylene-8-methyl-7-nonenal is the major aldehyde formed with Pt/Sn catalysts, regardless of the P-donor ligand used. This aldehyde is also the main product of the reaction catalyzed by the Rh/xantphos system (xantphos = 9,9-dimethyl-4,6-bis(diphenylphosphino)xantene). However, with ligands such as bisbi (bisbi = 2,2′-bis((diphenylphosphino)methyl)-1,1′-biphenyl), also with bite angles around 120°, but with more flexible backbones than xantphos, rhodium catalysts yield mainly cis- and trans-3-ethylidene-7-methyl-6-octenal. These two aldehydes are also formed in the reactions catalyzed by Rh and P-donor monodentate ligands or the bidentante ones with bite angles around 90° (dppe, dppp). For the last type of ligands, an increase in the flexibility of the backbone reduces the selectivity for the β,γ-unsaturated aldehydes.
Viaticene A – An Unusual Tetraterpene Cuticular Lipid Isolated from the Springtail Hypogastrura viatica
Bello, Jan E.,Stamm, Patrick,Leinaas, Hans Petter,Schulz, Stefan
supporting information, p. 2158 - 2162 (2019/03/17)
The cuticles of springtails are extremely wear- and friction-resistant, super-hydrophobic, non-fouling, and self-cleaning. As such, the chemistry of the lipids covering these cuticles is of great interest as a model for biomimetic super-hydrophobic surfaces, although only few of these lipids have been structurally elucidated. Hypogastrura viatica, a surface-dwelling springtail, produces highly branched tetraterpene hydrocarbons with an unprecedented [6+2]-terpene connectivity as components of the epicuticular lipid layer. The structure of the major lipid component, viaticene A, was elucidated through isolation, spectroscopic analysis, chemical derivatization, synthesis, as well as stereochemical analysis of the core unit obtained from ozonolysis of the isolated lipid. Viaticenes A and B represent a new class of irregular tetraterpenoid natural products.
