70681-74-2Relevant academic research and scientific papers
Synthesis of new azapolycyclic scaffolds via the domino aminolysis of dicyclopentadiene diepoxide in water
Palchykov, Vitalii A.,Gaponova, Rita G.,Omelchenko, Iryna V.,Kasyan, Liliya I.
, (2020)
A convenient method is reported for the multigram scale synthesis of compounds containing the novel octahydro-1H-2,5-epimino-4,7-methanoindene azapolycyclic system in good yields. This method involves the domino aminolysis of readily available dicyclopentadiene diepoxide in water at 165 °C. 2D NMR and XRD spectra of the products were studied in detail.
Substrate-induced diastereoselectivity in the dimethyldioxirane epoxidation of simple alkenes and dienes
Asouti,Hadjiarapoglou
, p. 1847 - 1850 (2007/10/03)
Various alkenes and dienes, such as (R)- or (S)-limonene 2, 2-carene 6, 3-carene 8, (R)-α-pinene 10, (S)-α-pinene 12, and endo-dicyclopentadiene 14 were transformed into the corresponding mono- and bis-epoxides by epoxidation with dimethyldioxirane (as an acetone solution). The selectivity observed in these epoxidations is explained by the assumption of hydrogen bonding between bridge protons and the dioxirane.
Regioselective and diastereoselective dimethyldioxirane epoxidation of substituted norbornenes and hexamethyl Dewar benzene
Asouti, Amalia,Hadjiarapoglou, Lazaros P.
, p. 539 - 542 (2007/10/03)
Various substituted norbornenes, such as endo-dicyclopentadiene 1, exo- dicyclopentadiene 5, 5-methylenebicyclo[2.2.1]hept-2-ene 8 and hexamethyl Dewar benzene 10 were transformed into the corresponding mono- and bis- epoxides by epoxidation with dimethyldioxirane (as an acetone solution).
Effect Of The Medium On The Methanolysis Of Dicyclopentadiene Diepoxide
Kas'yan, L. I.,Gaponova, R. G.,Okovityi, S. I.
, p. 733 - 740 (2007/10/02)
The reaction of dicyclopentadiene diepoxide with methanol was studied by molecular mechanics and semiempirical quantum-chemical calculations.It was shown that the nature of the medium has an effect on the rate and direction of the reaction.In the presence of sodium methoxide chemo-, regio-, and stereoselective opening of the epoxycyclopentane fragment occurs; the direction of the reaction is controlled by the steric factor.In the case of acid-catalyzed methanolysis the reaction rate is increased, and both epoxide fragments are transformed; methanolysis is accompanied by intramolecular cyclization as a result of nucleophilic attack by the methoxy group from the endo region of the norbornane fragment.
Oxidation of Organic Substrates by Molecular Oxygen/Aldehyde/ Heteropolyoxometalate System
Hamamoto, Masatoshi,Nakayama, Kouichi,Nishiyama, Yutaka,Ishii, Yasutaka
, p. 6421 - 6425 (2007/10/02)
Heteropolyoxometalate-catalyzed oxidations of organic compounds such as olefins and cyclic ketones with molecular oxygen in the presence of an aldehyde were examined.Olefins were epoxidized with dioxygen in the presence of 2 equiv of 2-methylpropanal under the influence of a catalytic amount of the mixed heteropolyoxometalate NPV6Mo6 (3) to give the corresponding epoxides in moderate to good yields.This catalytic oxidation method was also applied to the epoxidation of allylic and homoallylic alcohols.In the absence of olefins, the aldehydes were efficiently convertedinto the corresponding carboxylic acids.In addition, the Baeyer-Villiger oxidation of cyclic ketones was accomplished by using benzaldehyde instead of 2-methylpropanal as the aldehyde.
Dicyclopentadiene Oxidation. II. Catalyzed Liquid-Phase Oxidation of Dicyclopentadiene
Schnurpfeil, D.
, p. 842 - 847 (2007/10/02)
The liquid-phase oxidation of dicyclopentadiene 1 by molecular oxygen was studied in the presence of MoO2(acac)2 as a typical epoxidation catalyst.The yield of the mono-epoxides 2 and 3 is increased to 56.4 percent (uncatalyzed reaction: 43.6 percent).The ratio of the two mono-epoxides is decreased to 2/3 = 2.6 in relation to the uncatalyzed reaction 2/3 = 7.1).The influence of temperature, conversion and solvents is described.The bisepoxide 4 is formed at lower conversions than in the uncatalyzed reaction.But also at higher conversion of 1 not more than 10 percent of the bisepoxide 4 is formed.
Dicyclopentadiene Oxidation I. Uncatalyzed Liquid-Phase Oxidation of Dicyclopentadiene
Schnurpfeil, D.
, p. 481 - 488 (2007/10/02)
Dicyclopentadiene is oxidized by molecular oxygen to a mixture of the monoepoxides 2 and 3.The identification of the epoxides 2, 3 and 4 was executed with authentic samples prepared by epoxidation with peracetic acid or with tert-butylhydroperoxide in the presence of MoO2(acac)2.The main product is the substituted norbornene oxide 2.Allylic oxidation is also observed.Remarkable amounts of hydroperoxides can be determined iodometrically.The formation of allylic oxidation products 7, 8, 9 and 10 was proved by GC-MS-analysis.It is shown that in the uncatalyzed liquid phase oxidation of dicyclopentadiene no more than 50 percent of epoxides are formed.The bisepoxide 4 was found in small amounts only at higher conversions of the dicyclopentadiene.
