772-36-1Relevant articles and documents
Biomimetic conversion of α-pinene with H2O2 to sobrerol over V2O5: Dihydroxylation by a peroxo vanadium peracid vectoring gentle synergistic oxidation
He, Huiting,Huang, Geng,Kirk, Steven Robert,Li, Hui,Liu, Jian,Liu, Qiang,Liu, Xianxiang,Mao, Liqiu,Su, Shengpei,Xu, Qiong,Yin, Dulin
, (2020/05/18)
In this communication, we report the gentle preparation of sobrerol from dihydroxylation of α-pinene synergistically catalyzed by V2O5-H2O2 under benign conditions. It was proposed that a “peroxo vanadium acid”, VVO(OH)(OOH), was formed by HOO? insertion and proton transfer between V2O5 and H2O2. Theoretical DFT calculations that using the dimer?vanadium peracid as a model of the catalytically active species revealed that peroxo vanadium acid exhibited bifunctional catalytic capabilities resembling epoxidation of α-pinene by peracetic acid and then open-ring hydration with an acetic media.
Unique salt effect on highly selective synthesis of acid-labile terpene and styrene oxides with a tungsten/Hcatalytic system under acidic aqueous conditions
Hachiya, Houjin,Kon, Yoshihiro,Ono, Yutaka,Takumi, Kiyoshi,Sasagawa, Naoki,Ezaki, Yoichiro,Sato, Kazuhiko
experimental part, p. 1672 - 1678 (2012/07/16)
Acid-labile epoxides such as terpene and styrene oxides are effectively synthesized in high yields with good selectivities using tungsten-catalyzed hydrogen peroxide epoxidation in the presence of NaO The salt effect is thought to originate with the addition of a saturated amount of NaOto aqueous H this addition strongly inhibited the undesired hydrolysis of the acid-labile epoxy products, despite the biphasic conditions of substrate as oil phase and Has acidic aqueous phase.
Phosphotungstic acid as a versatile catalyst for the synthesis of fragrance compounds by α-pinene oxide isomerization: Solvent-induced chemoselectivity
Da Silva Rocha, Kelly A.,Hoehne, Juliana L.,Gusevskaya, Elena V.
body text, p. 6166 - 6172 (2009/06/17)
The remarkable effect of the solvent on the catalytic performance of H 3PW12O40, the strongest heteropoly acid in the Keggin series, allows direction of the transformations of α-pinene oxide (1) to either campholenic aldehyde (2), trans-carveol (3), trans-sobrerol (4a), or pinol (5). Each of these expensive fragrance compounds was obtained in good to excellent yields by using an appropriate solvent. Solvent polarity and basicity strongly affect the reaction pathways: nonpolar nonbasic solvents favor the formation of aldehyde 2; polar basic solvents favor the formation of alcohol 3; whereas in polar weakly basic solvents, the major products are compounds 4a and 5. On the other hand, in 1,4-dioxane, which is a nonpolar basic solvent, both aldehyde 2 and alcohol 3 are formed in comparable amounts. The use of very low catalyst loading (0.005-1 mol%) and the possibility of catalyst recovery and recycling without neutralization are significant advantages of this simple, environmentally benign, and low-cost method. This method represents the first example of the synthesis of isomers from α-pinene oxide, other than campholenic aldehyde, with a selectivity that is sufficient for practical usage.
