18315-83-8Relevant articles and documents
Iron(III) nitrate-induced aerobic and catalytic oxidative cleavage of olefins
Amaya, Toru,Fujimoto, Hayato
supporting information, p. 2657 - 2660 (2018/06/04)
Microwave-assisted catalytic oxidative cleavage of olefins using Fe(NO3)3·9H2O under O2 is reported. This reaction system is particularly effective when 9-benzylidene-9H-fluorene derivatives are used as substrates even though they are tri- and tetra-substituted olefins.
PREPARATION OF ALDEHYDES AND KETONES FROM ALKENES USING POLYOXOMETALATE CATALYSTS AND NITROGEN OXIDES
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Paragraph 0115, (2017/03/21)
The present invention relates to a process for preparing aldehydes and ketones by carbon-carbon bond cleavage of alkenes, wherein the process is catalysed by first row transition metal nitro coordinated polyoxometalate catalyst. The catalyst can be prepared by pre-treatment of aqua coordinated polyoxometalates with NO2, or they are formed in situ when the reactions are carried in nitroalkanes under aerobic conditions, or they are formed in situ from nitrosyl (NO) compounds in the presence of O2.
Aerobic carbon-carbon bond cleavage of alkenes to aldehydes catalyzed by first-row transition-metal-substituted polyoxometalates in the presence of nitrogen dioxide
Rubinstein, Amir,Jiménez-Lozanao, Pablo,Carbó, Jorge J.,Poblet, Josep M.,Neumann, Ronny
, p. 10941 - 10948 (2014/08/18)
A new aerobic carbon-carbon bond cleavage reaction of linear di-substituted alkenes, to yield the corresponding aldehydes/ketones in high selectivity under mild reaction conditions, is described using copper(II)-substituted polyoxometalates, such as {α2-Cu(L)P2W 17O61}8- or {[(Cu(L)]2WZn(ZnW 9O34)2}12-, as catalysts, where L = NO2. A biorenewable-based substrate, methyl oleate, gave methyl 8-formyloctanoate and nonanal in >90% yield. Interestingly, cylcoalkenes yield the corresponding epoxides as products. These catalysts either can be prepared by pretreatment of the aqua-coordinated polyoxometalates (L = H 2O) with NO2 or are formed in situ when the reactions are carried with nitroalkanes (for example, nitroethane) as solvents or cosolvents. Nitroethane was shown to release NO2 under reaction conditions. 31P NMR shows that the Cu-NO2-substituted polyoxometalates act as oxygen donors to the C-C double bond, yielding a Cu-NO product that is reoxidized to Cu-NO2 under reaction conditions to complete a catalytic cycle. Stoichiometric reactions and kinetic measurements using {α2-Co(NO2)P2W17O 61}8- as oxidant and trans-stilbene derivatives as substrates point toward a reaction mechanism for C-C bond cleavage involving two molecules of {α2-Co(NO2)P2W 17O61}8- and one molecule of trans-stilbene that is sufficiently stable at room temperature to be observed by 31P NMR.
