5604-55-7Relevant articles and documents
Regioselective alkene carbon-carbon bond cleavage to aldehydes and chemoselective alcohol oxidation of allylic alcohols with hydrogen peroxide catalyzed by [cis-Ru(II)(dmp)2(H2O)2] 2+ (dmp = 2,9-dimethylphenanthroline)
Kogan, Vladimir,Quintal, Miriam M.,Neumann, Ronny
, p. 5039 - 5042 (2007/10/03)
(Chemical Equation Presented) [cis-Ru(II)(dmp)2(H 2O)2]2+ (dmp = 2,9-dimethylphenanthroline) was found to be a selective oxidation catalyst using hydrogen peroxide as oxidant. Thus, primary alkenes were very efficiently oxidized via direct carbon-carbon bond cleavage to the corresponding aldehydes as an alternative to ozonolysis. Secondary alkenes were much less reactive, leading to regioselective oxidation of substrates such as 4-vinylcyclohexene and 7-methyl-1,6-octadiene at the terminal position. Primary allylic alcohols were chemoselectively oxidized to the corresponding allylic aldehydes, e.g., geraniol to citral.
Two-phase Hydroformylation of Buta-1,3-diene and Hydrocarbon Mixtures Containing Buta-1,3-diene
Fell, Bernhard,Hermanns, Peter,Bahrmann, Helmut
, p. 459 - 467 (2007/10/03)
The two-phase hydroformylation of buta-1,3-diene with (HRh(CO)[P(m-C6H4SO3Na) 3]3) the Kuntz catalyst system with excess P(m-C6H4SO3Na)3) gives high yields of C5-monoaldehydes. Main product in this mixture is the reactive trans- and cis-pent-3-enal. In consecutive reactions the pent-3-enal is partially hydrogenated to n-pentanal, but also - favoured by the protolytic milieu of the two-phase reaction - aldol condensated to 2-propenylheptadienal. The hydrogenation product of the propenylheptadienal, 2-propylheptanol-1, is a good plasticizer alcohol with a wanted low vapour pressure. Especially promising is the two-phase hydroformylation of the unrefined C4-fraction of the naphtha pyrolysis: after a more than 95 per cent conversion of the buta-1,3-diene also more than 80 per cent of the n-but-1-ene in the C4-fraction is hydroformylated mainly to wanted n-pentanal. Less than 5-10% of the n-but-2-enes and the isobutene in the C4-fraction react under these conditions to oxo-products (2- and 3-methylbutanal). Acetylenic compounds in the C4-fraction are converted quantitatively into products.
Asymmetric hydroformylation of conjugated dienes catalysed by [(R)-2-diphenylphosphino-1,1′-dinaphthalen-2′-yl] [(S)-1,1′-dinaphthalene-2,2′-diyl]phosphite-rhodium(I)
Horiuchi, Toshihide,Ohta, Tetsuo,Nozaki, Kyoto,Takaya, Hidemasa
, p. 155 - 156 (2007/10/03)
Asymmetric hydroformylation of conjugated dienes such as vinylcyclohexene, (E)-phenyl-buta-1,3-diene and 4-methyl-penta-1,3-diene using BINAPHOS-RhI complexes as catalysts {(R,S)-BINAPHOS = [(R)-2-diphenylphosphino-1,1′-dinaphthalen-2′-yl] [(S)-1,1′-dinaphthalene-2,2′-diyl]-phosphite} gives optically active β,γ-unsaturated aldehydes in high regio- (81-91%) and enantio-selectivities (84-97% ee).
