Relevant bibliographies by topics / Ring-strained alkenes

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  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters

Academic literature on the topic 'Ring-strained alkenes'

Author: Grafiati
Published: 22 July 2024
Last updated: 31 July 2025

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Journal articles on the topic "Ring-strained alkenes"

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Jeganmohan, Masilamani, and Pinki Sihag. "Recent Advances in Transition-Metal-Catalyzed C–H Functionalization Reactions Involving Aza/Oxabicyclic Alkenes." Synthesis 53, no. 18 (2021): 3249–62. http://dx.doi.org/10.1055/a-1528-1711.

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AbstractBicyclic alkenes, including oxa- and azabicyclic alkenes, readily undergo activation with facial selectivity in the presence of transition-metal complexes. This is due to the intrinsic angle strain on the carbon–carbon double bonds in such unsymmetrical bicyclic systems. During the past decades considerable progress has been made in the area of ring opening of bicyclic strained rings by employing the concept of C–H activation. This short review comprehensively compiles the various C–H bond activation assisted reactions of oxa- and azabicyclic alkenes, viz., ring-opening reactions, hydr
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Nishimura, T., T. Hayashi, E. Tsurumaki, T. Kawamoto, and X. X. Guo. "Enantioselective Desymmetrization via Ring Opening of Strained Alkenes." Synfacts 2008, no. 11 (2008): 1191. http://dx.doi.org/10.1055/s-0028-1083422.

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Sanzone, Jillian R., and K. A. Woerpel. "High Reactivity of Strained Seven-Membered-Ring trans -Alkenes." Angewandte Chemie International Edition 55, no. 2 (2015): 790–93. http://dx.doi.org/10.1002/anie.201510056.

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Sanzone, Jillian R., and K. A. Woerpel. "High Reactivity of Strained Seven-Membered-Ring trans -Alkenes." Angewandte Chemie 128, no. 2 (2015): 800–803. http://dx.doi.org/10.1002/ange.201510056.

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Feng, Qiang, Qian Wang, and Jieping Zhu. "Oxidative rearrangement of 1,1-disubstituted alkenes to ketones." Science 379, no. 6639 (2023): 1363–68. http://dx.doi.org/10.1126/science.adg3182.

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The Wacker process, which is widely used to convert monosubstituted alkenes into the corresponding methyl ketones, is thought to proceed through a Pd II /Pd 0 catalytic cycle involving a β-hydride elimination step. This mechanistic scenario is inapplicable to the synthesis of ketones from the 1,1-disubstituted alkenes. Current approaches based on semi -pinacol rearrangement of Pd II intermediates are limited to the ring expansion of highly strained methylene cyclobutane derivatives. Herein, we report a solution to this synthetic challenge by designing a Pd II /Pd IV catalytic cycle incorporati
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Shahid, Shereena, Muhammad Faisal, Aamer Saeed, et al. "A Review on the Scope of TFDO-Mediated Oxidation in Organic Synthesis-- Reactivity and Selectivity." Current Organic Synthesis 15, no. 8 (2018): 1091–108. http://dx.doi.org/10.2174/1570179415666180831104324.

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Dioxiranes are three-membered strained ring peroxides that are typical archetype examples of electrophilic entities. A dioxirane-based oxidant named 3-methyl(trifluoromethyl)dioxirane (TFDO) is a fluorinated analogue of the extremely valuable oxidant dimethyldioxirane (DMDO). Owing to the strained threemembered ring and presence of electron-withdrawing trifluoromethyl group, TFDO is several times more reactive than DMDO and acts as a significant chemical reagent. Moreover, TFDO exhibits high regio-, chemo- and stereo-selectivity even under unusual reaction conditions, i.e. at pH values close t
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Ma, Jiajia, Shuming Chen, Peter Bellotti, et al. "Facile access to fused 2D/3D rings via intermolecular cascade dearomative [2 + 2] cycloaddition/rearrangement reactions of quinolines with alkenes." Nature Catalysis 5, no. 5 (2022): 405–13. http://dx.doi.org/10.1038/s41929-022-00784-5.

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AbstractHybrid fused two-dimensional/three-dimensional (2D/3D) rings are important pharmacophores in drugs owing to their unique structural and physicochemical properties. Preparation of these strained ring systems often requires elaborate synthetic effort and exhibits low efficiency, thus representing a limiting factor in drug discovery. Here, we report two types of energy-transfer-mediated cascade dearomative [2 + 2] cycloaddition/rearrangement reactions of quinoline derivatives with alkenes, which provide a straightforward avenue to 2D/3D pyridine-fused 6−5−4−3- and 6−4−6-membered ring syst
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Sorensen, T. S., and F. Sun. "cis-2,3-Di-tert-butylcyclopropanones." Canadian Journal of Chemistry 75, no. 7 (1997): 1030–40. http://dx.doi.org/10.1139/v97-123.

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The preparation of the strained cis-2,3-di-tert-butylcyclopropanone 2 from the acyclic compound, α,α′-dibromodineopentyl ketone 1, using a previously reported methodology, is dramatic evidence of both the existence of oxyallyl intermediates in the mechanism of this reaction, and of the integrity with which oxyallyls ring-close to cyclopropanones by a disrotatory route. Because of the bulky cis substituents, cyclopropanone 2 exhibits a number of unusual spectroscopic features (as compared to the trans isomer 5). With the aid of ab initio calculations on 2 and 5, it can be shown that the C2—C3 b
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Boutin, Rebecca, Samuel Koh, and William Tam. "Recent Advances in Transition Metal-Catalyzed Reactions of Oxabenzonorbornadiene." Current Organic Synthesis 16, no. 4 (2019): 460–84. http://dx.doi.org/10.2174/1570179416666181122094643.

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Background: Oxabenzonorbornadiene (OBD) is a useful synthetic intermediate capable of undergoing multiple types of transformations due to three key structural features: a free alkene, a bridged oxygen atom, and a highly strained ring system. Most notably, ring-opening reactions of OBD using transition metal catalysts and nucleophiles produce multiple stereocenters in a single step. The resulting dihydronaphthalene framework is found in many natural products, which have been shown to be biologically active. Objective: This review will provide an overview of transition metal-catalyzed reactions
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Wanapun, D., K. A. Van Gorp, N. J. Mosey, M. A. Kerr, and T. K. Woo. "The mechanism of 1,3-dipolar cycloaddition reactions of cyclopropanes and nitrones — A theoretical study." Canadian Journal of Chemistry 83, no. 10 (2005): 1752–67. http://dx.doi.org/10.1139/v05-182.

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The 1,3-dipolar cycloaddition reaction of cyclopropanes and nitrones to give tetrahydro-1,2-oxazine has been studied with density functional theory calculations at the B3LYP/6-31+G(d,p) level of theory. Realistic substituents were modelled including those at the 2-, 3-, 4-, and 6-positions of the final oxazine ring product. The strained σ bond of the cyclopropane was found to play the role of an alkene in a conventional [3+2] dipolar cycloaddition. Two distinct, but similar, reaction mechanisms were found — an asymmetric concerted pathway and a stepwise zwitterionic pathway. The reaction barri
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Dissertations / Theses on the topic "Ring-strained alkenes"

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(2516944), Guangxing Sun. "Construction of n-bridged molecular ribbons and cavities." Thesis, 2000. https://figshare.com/articles/thesis/Construction_of_n-bridged_molecular_ribbons_and_cavities/26343832.

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<p dir="ltr">This thesis presents the most comprehensive approach to the synthesis of structures containing fused 7-azanorbornanes yet described. In particular, many of the high pressure reactions involving the cycloaddition of pyrroles and isoindoles to ring-strained alkenes, especially those involving norbornenes, are new and extremely versatile. Methods have been developed to control the stereoselectivity of these cycloadditions and many new molecular architectures such as I, II have been produced.</p><p dir="ltr">The other major contribution discovered in this area has been the preparation
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Book chapters on the topic "Ring-strained alkenes"

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Taber, Douglass. "Alkene Metathesis: Synthesis of Panaxytriol (Lee), Isofagomine (Imahori and Takahata), Elatol (Stoltz), 5-F2t -Isoprostane (Snapper), and Ottelione B (Clive)." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0030.

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Alkene metathesis has been used to prepare more and more challenging natural products. The first and second generation Grubbs catalysts 1 and 2 and the Hoveyda catalyst 3 are the most widely used. Daesung Lee of the University of Illinois at Chicago designed (Organic Lett. 2008, 10, 257) a clever chain-walking cross metathesis, combining 4 and 5 to make 6. The diyne 3 was carried on (3R, 9R, 10R )-Panaxytriol 7. Tatsushi Imahori and Hiroki Takahata of Tohoku Pharmaceutical University found (Tetrahedron Lett. 2008, 49, 265) that of the several derivatives investigated, the unprotected alcohol 8
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Taber, Douglass F. "The Williams Synthesis of (-)-4-Hydroxydictyolactone." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0083.

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(-)-4-Hydroxydictyolactone 3, representative of the cyclononene xenicanes isolated from the Dictyotacae algae, readily isomerizes thermally to the more stable ( Z )- 6,7-isomer. Attempts to directly form this strained ring system appeared to be fraught with difficulty. David R. Williams of Indiana University envisoned (J. Am. Chem. Soc. 2009, 131, 9038) that use of Suzuki coupling might ameliorate some of the strain, since at the point of commitment to bond formation, the Pd center would be included in the forming ring. This analysis led specifically to the trans ether 1, as cyclization of the
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Taber, Douglass. "The Hoveyda Synthesis of (-)-Clavirolide C." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0098.

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Conjugate addition-enolate trapping, a strategy originally developed by Gilbert Stork, has become a powerful method for stereocontrolled ring construction. A key step in the synthesis of (-)-Clavirolide C 3 reported (J. Am. Chem. Soc. 2008, 130, 12904) by Amir H. Hoveyda of Boston College occurred early on, with the enantioselective conjugate addition of Me3 Al to 1 to give the silyl enol ether 2. Enantioselective conjugate addition to establish a quaternary center β on a cyclohexanone had been established (OHL August 18, 2008), but not yet on cyclopentanones. Professor Hoveyda found that a mo
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Taber, Douglass. "The Paquette Synthesis of Fomannosin." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0096.

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The compact sesquiterpene ( + )-fomannosin 3, isolated from the pathogenic fungus Fomes annonsus, presents an interesting set of challenges for the organic synthesis chemist, ranging from the strained cyclobutene to the easily epimerized cyclopentanone. In the synthesis of 3 developed (J. Org. Chem . 2008, 73, 4548) by Leo A. Paquette of Ohio State University, the cyclopentane was constructed by ring-closing metathesis of 1. The real challenge of the synthesis was the enantiospecific preparation of 1 from D-glucose. The starting point for the preparation of 1 was the glucose derivative 4. Sele
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Taber, Douglass F. "Functional Group Protection: The Pohl Synthesis of β-1,4-Mannuronate Oligomers." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0015.

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D. Srinivasa Reddy of the National Chemical Laboratory converted (Org. Lett. 2015, 17, 2090) the selenide 1 to the alkene 2 under ozonolysis conditions. Takamitsu Hosoya of the Tokyo Medical and Dental University found (Chem. Commun. 2015, 51, 8745) that even highly strained alkynes such as 4 can be generated from a sulfinyl vinyl triflate 3. An alkyne can be protected as the dicobalt hexacarbonyl complex. Joe B. Gilroy and Mark S. Workentin of the University of Western Ontario found (Chem. Commun. 2015, 51, 6647) that following click chemistry on a non-protected distal alkyne, deprotection of
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Taber, Douglass F. "The Nicolaou Synthesis of (+)-Hirsutellone B." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0089.

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(+)-Hirsutellone B 3, isolated from the insect pathogenic fungus Hirsutella nivea BCC 2594, shows good activity (MIC = 0.78 μg/mL) against Mycobacterium tuberculosis. Approaching the synthesis of 3, K. C. Nicolaou of Scripps/La Jolla envisioned and reduced to practice (Angew. Chem. Int. Ed. 2009, 49, 6870) a spectacular tandem intramolecular epoxide opening: internal Diels-Alder cyclization (1 2) that established all three of the carbocyclic rings of 3 with the proper relative and absolute configuration. The construction of 1 began with commercial ( R) -(+)-citronellal 4. Wittig homologation e
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