35211-67-7Relevant academic research and scientific papers
Lanthanoid-catalysed Tishchenko reaction of mono- or di-aldehydes
Onozawa, Shun-Ya,Sakakura, Toshiyasu,Tanaka, Masato,Shiro, Motoo
, p. 4291 - 4302 (1996)
Lanthanoid complexes are found to be very active catalysts for the Tishchenko reaction of aldehydes. In the presence of Cp*2LnCH(SiMe3)2 (Ln = Nd, La), esters are obtained from corresponding monoaldehydes in high yields. This method is applicable to dialdehydes. The reaction of o-phthalaldehyde proceeds intramolecularly to give phthalide quantitatively. Terephthalaldehyde and di(4-formylphenyl) ether are cleanly converted into the poly[p-(carboxymethylene)phenylene] (II) and poly[p-(carboxymethylene)(p-phenylenoxy)phenylene] (III), respectively. On the other hand, isophthalaldehyde polymerizes first and then the polymer is transformed into a macrocyclic lactone 1,5,11-trioxo-2,4;8,10;14,16-tribenzo-6,12,18-trioxacyclooctadecane (1-a) in high yields. The 18-membered macrocyclic structure of 1-a was determined by the X-ray analysis. Stoichiometric reactions of the La complex with benzaldehyde indicated the intermediacy of alkoxo complexes in the catalysis.
Synthesis of β,γ-unsaturated ketones from acid chlorides through carbon-pentamethylcyclopentadienyl bond formation and cleavage
Uemura, Minoru,Iwasaki, Masayuki,Morita, Eiji,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 2400 - 2405 (2009/09/26)
Reaction of acid chlorides with lithium pentamethylcyclopentadienide afforded the corresponding pentamethyl-cyclopentadienyl ketones in high yield. These ketones were treated with an allylaluminum reagent to form the corresponding 3-butenyl alcohols. Removal of pentamethylcyclopentadiene upon heating or treatment with a catalytic amount of trichloroacetic acid yielded the corresponding β,γ-unsaturated ketones in good yields.
Synthesis of β,γ-unsaturated ketones by allylation of pentamethylcyclopentadienyl ketones followed by removal of pentamethylcyclopentadiene
Iwasaki, Masayuki,Morita, Eiji,Uemura, Minoru,Yorimitsu, Hideki,Oshima, Koichiro
, p. 167 - 169 (2008/03/13)
A new route to β,γ-unsaturated ketones is disclosed. Aryl pentamethylcyclopentadienyl ketones underwent allylation with allyldimethylaluminum to yield the corresponding alcohols. Heating the alcohols in boiling toluene resulted in removal of pentamethylcy
