Academic literature on the topic 'Acetylenic ketones'

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Journal articles on the topic "Acetylenic ketones"

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Shvartsberg, M. S., and L. G. Fedenok. "Isomerization of ?-acetylenic ketones." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 39, no. 9 (September 1990): 1906–10. http://dx.doi.org/10.1007/bf00958259.

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Zanina, A. S., S. I. Shergina, I. E. Sokolov, and I. L. Kotlyarevskii. "Synthesis of acetylenic ketones." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 39, no. 11 (November 1990): 2307–11. http://dx.doi.org/10.1007/bf00958843.

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Taniguchi, Mikio, Shozo Kobayashi, Masako Nakagawa, Tohru Hino, and Yoshito Kishi. "β-Halovinyl ketones: Synthesis from acetylenic ketones." Tetrahedron Letters 27, no. 39 (January 1986): 4763–66. http://dx.doi.org/10.1016/s0040-4039(00)85059-5.

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Mai, Juri, and Sascha Ott. "The Fascinating World of Phosphanylphosphonates: From Acetylenic Phosphaalkenes to Reductive Aldehyde Couplings." Synlett 30, no. 16 (August 13, 2019): 1867–85. http://dx.doi.org/10.1055/s-0039-1690129.

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This account highlights the versatility of phosphanylphosphonates, which can be used for the preparation of phosphorus-containing π-systems and as reagents for the reductive coupling of carbonyl compounds to alkenes. Phosphanylphosphonates with metal fragments coordinated to the P-lone pair have been known for a long time and they have been used for the synthesis of phosphaalkenes by means of the phospha-Horner–Wadsworth–Emmons reaction. With the original aim of incorporating phosphorus heteroatoms into classical all-carbon ethynylethene scaffolds, we entered the field of phosphanylphosphonates with the discovery that these compounds engage in complex cascade reactions with acetylenic ketones, forming 1,2-oxaphospholes, cumulenes, and bisphospholes. Later, we synthesized the first metal-free phosphanylphosphonate, which reacts with aldehydes to yield phosphaalkenes, but gives phospholones when diacetylenic ketones are used as substrates. In the final part of the account, we outline our discovery and the development of an unprecedented carbonyl–carbonyl cross-coupling reaction. This protocol offers a straightforward method for the synthesis of nonsymmetric 1,2-disubstituted alkenes directly from two dissimilar aldehydes.1 Combining Acetylenes with Phosphaalkenes2 Synthetic Examples of Acetylenic Phosphaalkenes3 The Phospha-Horner–Wadsworth–Emmons Approach to Phosphaalkenes3.1 Metal-Coordinated Phosphanylphosphonates3.2 Mechanism of the Phospha-Horner–Wadsworth–Emmons Reaction3.3 The First Metal-Free Phosphanylphosphonate and Its Reactivity with Aldehydes4 Reactions with Acetylenic Ketones4.1 Metal-Coordinated Phosphanylphosphonate and Monoacetylenic Ketones4.2 Metal-Coordinated Phosphanylphosphonate and Diacetylenic Ketones4.3 Metal-Free Phosphanylphosphonate and Diacetylenic Ketones5 Metal-Free Phosphanylphosphonate as a Coupling Reagent for Aldehydes6 E-Alkenes by the Reductive Coupling of Two Aldehydes7 Conclusions and Outlook
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Meng, Ling‐Guo, Pei‐Jie Cai, Qing‐Xiang Guo, and Song Xue. "Direct Iodination of Monosubstituted Aryl Acetylenes and Acetylenic Ketones." Synthetic Communications 38, no. 2 (January 2008): 225–31. http://dx.doi.org/10.1080/00397910701749724.

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Shergina, S. I., I. E. Sokolov, and A. S. Zanina. "Synthesis of fluorinated acetylenic ketones." Bulletin of the Russian Academy of Sciences Division of Chemical Science 41, no. 1 (January 1992): 127–28. http://dx.doi.org/10.1007/bf00863927.

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Fukuyama, Takahide, Ryo Yamaura, and Ilhyong Ryu. "Synthesis of acetylenic ketones by a Pd-catalyzed carbonylative three-component coupling reaction in [bmim]PF6." Canadian Journal of Chemistry 83, no. 6-7 (June 1, 2005): 711–15. http://dx.doi.org/10.1139/v05-031.

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A carbonylative three-component coupling reaction of aryl iodides with terminal alkynes catalyzed by PdCl2(PPh3)2 was carried out using an ionic liquid, [bmim]PF6, as the reaction medium, which resulted in good yields of α,β-acetylenic ketones. The low-viscosity ionic liquid, [bmim]NTf2, was not suitable for this reaction, since the background Sonogashira coupling reaction, a competing reaction, also proceeded.Key words: carbonylation, palladium, three-component coupling, ionic liquid, α,β-acetylenic ketones.
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Levashov, Andrey S., and Dmitrii S. Buryi. "Tetraalkynylstannanes in Synthesis of α,β-Acetylenic Ketones." Proceedings 9, no. 1 (November 14, 2018): 44. http://dx.doi.org/10.3390/ecsoc-22-05691.

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Akynyl ketones were synthesized from tetraalkinylstannanes and both aliphatic and aromatic acyl chlorides under Lewis acid catalysis. The structure of products was confirmed by means of NMR, IR, GC-MS. The method is suitable for the synthesis of long-chain acetylenic ketones.
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Sengee, Myagmarsuren, and Leiv K. Sydnes. "Specific conjugate addition to α,β-acetylenic ketones." Pure and Applied Chemistry 83, no. 3 (February 3, 2011): 587–96. http://dx.doi.org/10.1351/pac-con-10-10-24.

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A variety of α,β-unsaturated acetylenic ketones, prepared in good yields from 3,3,4,4-tetraethoxybut-1-yne (TEB), have been reacted with selected mono- and bis-nucleophilic reagents. The mononucleophiles react in a Michael fashion and give in most cases the corresponding α,β-unsaturated alkenones in good yield. Many of the alkenes are formed as single stereoisomers, but the configuration depends on the nature of the nucleophile. If hydrogen bonds can be formed, the Z geometry is preferred, otherwise the E geometry is completely predominant. Experiments have also uncovered that α,β-unsaturated acetylenic ketones with a gem-diethoxy moiety in the α' position decompose when reacted with sodium hydroxide in aqueous tetrahydrofuran (THF); the carbonyl group is attacked and a carboxylic acid and a terminal alkyne are formed. If the nucleophiles contain two nucleophilic centers or if the α,β-unsaturated acetylenic ketones contain an additional reactive group, such as a hydroxyl group or an acyloxy moiety, useful secondary reactions may occur. By taking advantage of such secondary transformations, two completely regioselective syntheses of furans have so far been developed.
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ZANINA, A. S., S. I. SHERGINA, I. E. SOKOLOV, and I. L. KOTLYAREVSKII. "ChemInform Abstract: Synthesis of Acetylenic Ketones." ChemInform 23, no. 27 (August 21, 2010): no. http://dx.doi.org/10.1002/chin.199227139.

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Dissertations / Theses on the topic "Acetylenic ketones"

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Catterick, David. "The parallel synthesis of natural product families." Thesis, University of Oxford, 1998. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.299756.

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Forest, Jeremy Scott. "Part 1: Synthesis of new camphor-based auxiliaries; Part 2: isomerization/cyclization of acetylenic ketones to cyclopentenones." Thesis, University of Hawaii at Manoa, 2003. http://hdl.handle.net/10125/6974.

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Part 1: Synthesis of New Camphor-Based Auxiliaries. The development of new camphor-based auxiliaries for an enantioselective route to cyclopentenones is discussed. Changes to the basic camphor auxiliary that was used in the original methodology were made, resulting in a series of seven new camphor-based chiral auxiliaries. These modifications were made with the hope of producing a new auxiliary capable of increasing the enantiomeric excesses of the cyclopentenone products. Synthetic routes to each auxiliary are provided along with the results of the cyclopentannelation reaction. Part 2: Isomerization I Cyclization of Acetylenic Ketones to Cyclopentenones Allenyl ketones are key intermediates in the formation of cyclopentenones by cyclopentannelation. A new method for the formation of allenyl ketones in situ is discussed. This has become an attractive method especially for the formation of racemic a-methylene cyclopentenones substituted at the exocyclic methylene. A convenient method for the production of the isolable acetylenic ketone precursors from various propargylic ether and morpholino enamide starting materials is discussed. The results of the in situ isomerization of the acetylenic ketones to their corresponding allenyl ketones and cyclopentenones are also accounted.
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Laboue, Blandine. "Preparation de cetones par acylation de composes organomanganeux : extension et amelioration de la methode." Paris 6, 1987. http://www.theses.fr/1987PA066464.

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Preparation des cetones acetyleniques fonctionnelles et de divers alcools tertiaires par acylation des composes organomagnesiens en presence de sels de manganese seuls ou associes a des sels de cuivre
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Parlier, Andrée. "Application des complexes carbeniques du tungstene a la synthese organique et organometallique." Paris 6, 1987. http://www.theses.fr/1987PA066570.

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Figadère, Bruno. "Les composes organomanganeux mixtes : addition 1-2 selective sur des aldehydes ou des cetones portant un groupe fonctionnel, enolisation regioselective de cetones : application en synthese." Paris 6, 1987. http://www.theses.fr/1987PA066371.

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Les reactifs organomanganeux rmnx(x=cl, br, i; r=n-, sec- t-alkyl, alcenyl, aryl, alcynyl) s'additionnent aux aldehydes et cetones fonctionnels pour donner selectivement les alcools correspondant avec d'excellents rendements. Les reactifs rmnz(z=nphme) enolisent les cetones avec une excellente regioselectivite. Les enolates manganeux ainsi prepares sont tres aisement acyles, silyles, alkyles, hydroxyalkyles, avec des rendements de 60% a 90%, a la temperature ambiante
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Book chapters on the topic "Acetylenic ketones"

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Shirakawa, S., and K. Maruoka. "Asymmetric Michael Addition of Cyanoacetates to Acetylenic Ketones." In Brønsted Base and Acid Catalysts, and Additional Topics, 1. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-205-00426.

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Schantl, J. G. "Reaction of Aryl- and Hetarylhydrazones with Alkenic and Acetylenic Dipolarophiles." In Heteroatom Analogues of Aldehydes and Ketones, 1. Georg Thieme Verlag KG, 2004. http://dx.doi.org/10.1055/sos-sd-027-00648.

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Pfeiffer, W. D. "From Acetylenic Ketones or Aldehydes and Hydroxylamine -Sulfonic Acid." In Five-Membered Hetarenes with One Chalcogen and One Additional Heteroatom, 1. Georg Thieme Verlag KG, 2002. http://dx.doi.org/10.1055/sos-sd-011-01332.

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Shirakawa, S., and K. Maruoka. "Asymmetric Michael Addition of β-Keto Esters to Acetylenic Ketones." In Brønsted Base and Acid Catalysts, and Additional Topics, 1. Georg Thieme Verlag KG, 2012. http://dx.doi.org/10.1055/sos-sd-205-00420.

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Schatz, J. "Reaction of Thioglycolates or α-Sulfanyl Ketones with Acetylenic Esters." In Fully Unsaturated Small-Ring Heterocycles and Monocyclic Five-Membered Hetarenes with One Heteroatom, 1. Georg Thieme Verlag KG, 2001. http://dx.doi.org/10.1055/sos-sd-009-00409.

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Li, Jie Jack, Chris Limberakis, and Derek A. Pflum. "Oxidation." In Modern Organic Synthesis in the Laboratory. Oxford University Press, 2008. http://dx.doi.org/10.1093/oso/9780195187984.003.0009.

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Activated manganese dioxide (MnO2) reliably oxidizes acetylenic, allylic, and benzylic alcohols to aldehydes and ketones. Saturated primary and secondary alcohols are also oxidized, albeit more slowly. The two main concerns are the activity of the manganese dioxide and the slow filtration of salts after the reaction. Activated MnO2 is available commercially or may be prepared. To a solution of 15.3 g (37.5 mmol) of the alcohol in 150 mL of hexanes was added 60 g of activated MnO2. The reaction mixture was stirred at 22 °C overnight and filtered, and the solid residue was washed with 30% EtOAc in hexanes solution. The combined filtrates were dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography on SiO2 (EtOAc:hexanes, 1:10) to give 13.7 g (90%) of the ketone as a colorless oil. Reference: Wipf, P.; Xu, W. J. Org. Chem. 1996, 61, 6556–6562. Chromium-based oxidations are reliable and well established, but the toxicity associated with chromium salts have meant that they are generally considered the second choice. For a review of chromium–amine complex oxidations, see Luzzio, F. A. Org. React. 1998, 53, 1-221. To a mixture of pyridinium chlorochromate (PCC 339 mg, 1.57 mmol), ammonium acetate (215 mg, 2.62 mmol), and 4 Å molecular sieves (610 mg) in CH2Cl2 (33 mL) was added a solution of the alcohol (208 mg, 1.05 mmol) in CH2Cl2 (14 mL) under argon at 0 °C over a period of 10 min. After the mixture had been stirred at room temperature for 3 h, diethyl ether (200 mL) was added and the mixture was filtered through a short pad of Florisil. The filtrate was washed successively with water (100 mL) and brine (100 mL), dried with Na2SO4, and concentrated. The residue was purified by chromatography on silica gel (hexane 70%, Et2O 30%) followed by distillation to give the aldehyde as a colorless oil (132 mg, 63%).
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Brandsma, Lambert. "Reactions with Aldehydes and Ketones." In Synthesis of Acetylenes, Allenes and Cumulenes, 119–34. Elsevier, 2004. http://dx.doi.org/10.1016/b978-012125751-4/50006-0.

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Trofimov, B. A., A. I. Mikhaleva, E. Yu Schmidt, and L. N. Sobenina. "Pyrroles and N-Vinylpyrroles from Ketones and Acetylenes." In Advances in Heterocyclic Chemistry, 209–54. Elsevier, 2010. http://dx.doi.org/10.1016/s0065-2725(10)09907-1.

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"Chapter 4. Derivatives from acetylene reacting with ketone." In Manufacture of Fine Chemicals from Acetylene, 111–52. De Gruyter, 2021. http://dx.doi.org/10.1515/9783110714999-004.

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"Synthesis of Pyrroles and N-Vinylpyrroles by the Reaction of Ketones (Ketoximes) with Acetylenes." In Chemistry of Pyrroles, 1–128. CRC Press, 2014. http://dx.doi.org/10.1201/b17510-2.

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Conference papers on the topic "Acetylenic ketones"

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Dotsenko, Victor, Andrey Levashov, Dmitriy Buriy, Valeriy Konshin, Inna Aksenova, and Nikolay Aksenov. "Oppenauer-type synthesis of α, β-acetylenic ketones from tetra(phenylethynyl)tin and aromatic aldehydes." In The 21st International Electronic Conference on Synthetic Organic Chemistry. Basel, Switzerland: MDPI, 2017. http://dx.doi.org/10.3390/ecsoc-21-04807.

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Reports on the topic "Acetylenic ketones"

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Brown, H. C., P. V. Ramachandran, S. A. Weissman, and S. Swaminathan. Selective Reductions. 46. Effect of the Steric Requirement at the 2- Position of Apopinene on Chiral Reductions. B-Iso-2-n-Propylapopinocampheyl-9- Borabicyclo(3.3.1)Nonane as Improved Reagents for the Chiral Reduction of Alpha, Beta-Acetylenic Ketones and Alpha-Keto Esters. Fort Belvoir, VA: Defense Technical Information Center, January 1991. http://dx.doi.org/10.21236/ada230919.

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