20507-57-7Relevant academic research and scientific papers
Asymmetric diene synthesis of bicyclo[2.2.2]octenes in the presence of Lewis acids
Mamedov,Mamedova,Gadzhieva,Nagiev
, p. 1376 - 1378 (2007)
Asymmetric diene synthesis of substituted bicyclo[2.2.2]octenes from (-)-menthyl acrylate and cyclohexa-1,3-diene in the presence of achiral Lewis acid catalysts (TiCl4, AlCl3, BBr3, AlCl 3·OEt2, BBr
Synthesis and computational analysis of conformationally restricted [3.2.2]- and [3.2.1]-3-azabicyclic diamines
Tummalapalli, Sreedhar Reddy,Bhat, Rohit,Waitt, Craig,Eshuis, Henk,Rotella, David P.
, p. 4087 - 4089 (2017/10/06)
Conformational restriction is a useful approach for ligand design in organic and medicinal chemistry. This manuscript reports the facile synthesis and in silico conformational analysis of two new diastereomeric [3.2.2]-3-azabicyclic, two new [3.2.1]-3-aza-8-oxy-bicyclic and one new [3.2.1]-3-azabicyclic diamine scaffolds. A conformational analysis of these structures along with calculation of carbon–carbon/carbon–nitrogen bond angles was carried out and compared to those in the flexible 1,3-diaminopropane template upon which they were based. It is of particular importance that these scaffolds have bond lengths and angles that can overlap with low energy conformers of the flexible diamine. Such information is useful for ligand design in organic chemistry and for development of structure activity relationships and in silico screening in medicinal chemistry.
BORON-BASED CYCLOADDITION CATALYSTS AND METHODS FOR THE PRODUCTION OF BIO-BASED TEREPHTHALIC ACID, ISOPHTHALIC ACID AND POLY (ETHYLENE TEREPHTHALATE)
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Paragraph 00171; 00187, (2017/04/11)
Methods for producing cycloaddition products comprising: reacting a diene with a dienophile in the presence of one or more boron-based catalysts of Formula I or Formula II are provided. In particular, the methods can be used to prepare 4-methyl-3-cyclohexene- 1-carboxylic acid and 3-methyl-3-cyclohexene-l-carboxylic acid, including bio-based versions thereof. The cycloaddition products can be advantageously used in the production of terephthalic acid and isophthalic acid, and ultimately, poly(ethylene terephthalate), and bio-based versions thereof. Formula I Formula II
Metal-free intramolecular cyclopropanation of alkenes through iodonium ylide methodology
Moriarty, Robert M.,Tyagi, Sachin,Kinch, Mark
experimental part, p. 5801 - 5810 (2010/09/18)
Intramolecular cyclopropanation of alkenes occurs thermally with iodonium ylides in the absence of conventional metal catalysts such as Rh(II) and Cu(II). In rigid molecular systems conversions are near quantitative. A mechanism is proposed involving formal 2+2 cycloaddition followed by reductive elimination of PhI to yield the cyclopropane. Intramolecular cyclopropanation of alkenes occurs thermally with iodonium ylides in the absence of conventional metal catalysts such as Rh(II) and Cu(II). In rigid molecular systems conversions are near quantitative. A mechanism is proposed involving formal 2+2 cycloaddition followed by reductive elimination of PhI to yield the cyclopropane.
Orbital unsymmetrization of olefins arising from non-equivalent orbital interactions. σ-π Coupling in bicyclo[2.2.2]octenes
Ohwada, Tomohiko,Uchiyama, Masanobu,Tsuji, Motonori,Okamoto, Iwao,Shudo, Koichi
, p. 296 - 306 (2007/10/03)
We characterized experimentally the substituent effect of a 5-exo substituent on the π facial selectivities of bicyclo[2.2.2]octenes toward electrophilic oxidative reactions such as epoxidation and dihydroxylation, and we discuss the underlying orbital interactions of vicinal σ orbitals and the olefinic π orbital involved in bicyclo[2.2.2]octenes, and commonly in methylenenorbornanes. Of significance is the out-of-phase motif of these σ- π couplings. Electron-withdrawing substituents such as cyano and carboxylic acid groups unequalize the relevant σ-π coupling, leading to the observed syn-facial preference. Alkyl substituents exhibit an electron-donative perturbing effect, depending on the bicyclic ring system.
Zirconocene-catalyzed cationic Diels-Alder reactions
Wipf, Peter,Xu, Wenjing
, p. 4551 - 4562 (2007/10/02)
In situ prepared Cp2ZrCl+ catalyzes the formation of dioxolenium ions from α,β-unsaturated epoxy esters. As a consequence of this activation process, acrylate, methacrylate and crotonate derivatives undergo a rapid and stereoselective cationic [4+2] cycloaddition with a wide range of dienes. Ring-extended carboxylic acid derivatives are formed in 1-7 h at 0-21°C and in 50-90% yield after saponification of the intermediate diol esters. Simple Lewis acid catalysis by Cp2ZrCl+ can be excluded on the basis of the experimental results.
216. Bicyclooctanes. Syntheses and Hydrolyses of 6-exo-substituted 2-exo- and 2-endo-Bicyclooctyl p-Toluenesulfonates. Part 9
Grob, Cyril A.,Sawlewicz, Pawel
, p. 1859 - 1867 (2007/10/02)
The synthesis of the title compounds and their hydrolysis products in 70percent dioxane are described.
Bicyclooctane-2,5-carbolactone
Brecknell, Douglas J.,Carman, Raymond M.,Day, Peter J.
, p. 2323 - 2329 (2007/10/02)
The title compound has been synthesized and compared with bicyclooctane-2,6-carbolactone.Ambiguities in the literature concerning the preparation of the title compound have been resolved.
