71911-71-2Relevant academic research and scientific papers
MCM-41-Quaternary organic tetraalkylammonium hydroxide composites as strong and stable Bronsted base catalysts
Rodriguez, Isabel,Iborra, Sara,Corma, Avelino,Rey, Fernando,Jorda, Jose L.
, p. 593 - 594 (1999)
Quaternary organic tetraalkylammonium hydroxide grafted on MCM-41 is a strong Bronsted base catalyst, and represents a useful alternative to soluble bases in reactions such as Knoevenagel condensations, Michael additions and aldol condensations because of their high catalytic activity under mild conditions, and good stability.
Malonate Anion Induced Favorskii-Type Rearrangement. Reaction of Cyclic α-Halo Ketones with Sodiomalonates
Sakai, Takashi,Amano, Eiichiro,Kawabata, Akifumi,Takeda, Akira
, p. 43 - 47 (2007/10/02)
The reaction of 2-chlorocyclohexanone (1b) with ethyl sodiomalonate in benzene at 0-25 deg C gave 6-bicyclohexan-6-ol (4c), the Favorskii-type intermediate, in 49percent yield, in place of the substitution product ethyl C-(2-oxocyclohexyl)malonate (3).Derivatives of bicycloheptan-7-ol (4a,b) and those of bicyclohexan-6-ol (4d,e) were also obtained in good yields by similar means.Compound 4c was transformed into 3 readily by heating with 0.05 equiv of NaH in benzene.The hydrolysis of 4a-d with 0.2 N NaOH followed by pyrolysis at 110-120 deg C gave the ring-contracted β-keto esters 9a-d.Pyrolysis after the hydrolysis with 2N NaOH gave the corresponding ketones 11a-d in good yields.Oxidation of 4c with CrO3 and HClO4 afforded ethyl C-(2-hydroxycyclopentanecarbonyl)malonate (14) in 45 percent yield.Treatment of 4c with Br2 gave ethyl C-(1-bromocyclopentanecarbonyl)malonate (18) in 64 percent yield.
