Relevant bibliographies by topics / Alkyne group

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Academic literature on the topic 'Alkyne group'

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Published: 24 April 2022

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Journal articles on the topic "Alkyne group"

1

Potapov, Vladimir A., Maxim V. Musalov, Evgeny O. Kurkutov, Vladimir A. Yakimov, Alfiya G. Khabibulina, Maria V. Musalova, Svetlana V. Amosova, Tatyana N. Borodina, and Alexander I. Albanov. "Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes." Molecules 25, no. 1 (January 3, 2020): 194. http://dx.doi.org/10.3390/molecules25010194.

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The original goal of this research was to study stereochemistry of selenium dihalides addition to cycloalkenes and properties of obtained products. Remarkable alkene-to-alkene and alkene-to-alkyne transfer reactions of selenium dibromide and PhSeBr were discovered during this research. The adducts of selenium dibromide with alkenes or cycloalkenes easily exchange SeBr2 with other unsaturated compounds, including acetylenes, at room temperature, in acetonitrile. Similar alkene-to-alkene and alkene-to-alkyne transfer reactions of the PhSeBr adducts with alkenes or cycloalkenes take place. The supposed reaction pathway includes the selenium group transfer from seleniranium species to alkenes or alkynes. It was found that the efficient SeBr2 and PhSeBr transfer reagents are Se(CH2CH2Br)2 and PhSeCH2CH2Br, which liberate ethylene, leading to a shift in equilibrium. The regioselective and stereoselective synthesis of bis(E-2-bromovinyl) selenides and unsymmetrical E-2-bromovinyl selenides was developed based on the SeBr2 and PhSeBr transfer reactions which proceeded with higher selectivity compared to analogous addition reactions of SeBr2 and PhSeBr to alkynes under the same conditions.
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Alexander, S. R., G. M. Williams, M. A. Brimble, and A. J. Fairbanks. "A double-click approach to the protecting group free synthesis of glycoconjugates." Organic & Biomolecular Chemistry 16, no. 8 (2018): 1258–62. http://dx.doi.org/10.1039/c8ob00072g.

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Alabugin, Igor, Edgar Gonzalez-Rodriguez, Rahul Kawade, Aleksandr Stepanov, and Sergei Vasilevsky. "Alkynes as Synthetic Equivalents of Ketones and Aldehydes: A Hidden Entry into Carbonyl Chemistry." Molecules 24, no. 6 (March 15, 2019): 1036. http://dx.doi.org/10.3390/molecules24061036.

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The high energy packed in alkyne functional group makes alkyne reactions highly thermodynamically favorable and generally irreversible. Furthermore, the presence of two orthogonal π-bonds that can be manipulated separately enables flexible synthetic cascades stemming from alkynes. Behind these “obvious” traits, there are other more subtle, often concealed aspects of this functional group’s appeal. This review is focused on yet another interesting but underappreciated alkyne feature: the fact that the CC alkyne unit has the same oxidation state as the -CH2C(O)- unit of a typical carbonyl compound. Thus, “classic carbonyl chemistry” can be accessed through alkynes, and new transformations can be engineered by unmasking the hidden carbonyl nature of alkynes. The goal of this review is to illustrate the advantages of using alkynes as an entry point to carbonyl reactions while highlighting reports from the literature where, sometimes without full appreciation, the concept of using alkynes as a hidden entry into carbonyl chemistry has been applied.
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Wang, Li-Sheng, and Martin Cowie. "Alkyne transformations at RhMn centres. Facile conversion between parallel and perpendicular alkyne binding modes and conversions to vinyl groups." Canadian Journal of Chemistry 73, no. 7 (July 1, 1995): 1058–71. http://dx.doi.org/10.1139/v95-131.

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The heterobinuclear complex [RhMn(CO)4(dppm)2] (1) (dppm = Ph2PCH2PPh2) reacts with alkynes (RC≡CR; R = CO2Me (DMAD), CF3 (HFB)) to yield the alkyne-bridged products [RhMn(CO)4(μ-RC2R)(dppm)2] (3a, 3b), in which the alkyne binds parallel to the metals. These species lose one carbonyl to yield two isomers in which the bridging alkyne group is either parallel or perpendicular to the Rh–Mn vector (4 or 5). Unusually facile interconversion between these two alkyne binding modes occurs. Protonation of the different alkyne-bridged species appears to occur at the metals with subsequent transfer to the alkyne ligand, yielding a series of vinyl complexes. These vinyl complexes are also obtained from the reaction of the hydride-bridged complex [RhMn(CO)4(μ-H)(dppm)2][BF4] (2) with alkynes. A related vinyl species [RhMn((CH3)C=CH2)(CO)4(dppm)2][BF4] (9a) is obtained in the reaction of 2 with allene. Also obtained in the allene reaction is the isomeric η1-allyl complex [RhMn(η1-CH2C(H)=CH2)(CO)4(dppm)2][BF4] (9b), which converts to 9a upon refluxing. The methyl analogues [RhMnCH3(CO)4(dppm)2][X] (X = SO3CF3, I) have been characterized and their structural formulations offer support for those of the vinyl species. Keywords: heterobinuclear, alkyne complexes, vinyl complexes.
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Benhamou, Laure, Daniel W. Walker, Dejan-Krešimir Bučar, Abil E. Aliev, and Tom D. Sheppard. "Synthesis of substituted benzooxaborinin-1-ols via palladium-catalysed cyclisation of alkenyl- and alkynyl-boronic acids." Organic & Biomolecular Chemistry 14, no. 34 (2016): 8039–43. http://dx.doi.org/10.1039/c6ob01419d.

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Ouyang, Xuan-Hui, Yang Li, Ren-Jie Song, Ming Hu, Shenglian Luo, and Jin-Heng Li. "Intermolecular dialkylation of alkenes with two distinct C(sp3)─H bonds enabled by synergistic photoredox catalysis and iron catalysis." Science Advances 5, no. 3 (March 2019): eaav9839. http://dx.doi.org/10.1126/sciadv.aav9839.

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The functionalization of unactivated C(sp3)─H bonds represents one of the most powerful and most atom-economical tools for the formation of new carbon-based chemical bonds in synthesis. Although cross-dehydrogenative coupling reactions of two distinct C─H bonds for the formation of carbon-carbon bonds have been well investigated, controlled functionalizations of two or more different C(sp3)─H bonds across a functional group or a molecule (e.g., an alkene or alkyne) in a single reaction remain challenging. Here, we present a three-component dialkylation of alkenes with common alkanes and 1,3-dicarbonyl compounds via synergistic photoredox catalysis and iron catalysis for the synthesis of two functionalized 1,3-dicarbonyl compounds. Mechanistic studies suggest that the photoredox catalysis serves as a promotion system to allow the dialkylation to proceed under mild conditions by reducing the oxidation and reduction potentials of the iron intermediates and the reaction partners.
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Vasilevsky, Sergei F., Maria P. Davydova, Victor I. Mamatyuk, Nikolay Tsvetkov, Audrey Hughes, Denis S. Baranov, and Igor V. Alabugin. "Full Cleavage of C≡C Bond in Electron-Deficient Alkynes via Reaction with Ethylenediamine." Australian Journal of Chemistry 70, no. 4 (2017): 421. http://dx.doi.org/10.1071/ch17026.

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Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C≡C bond even in the absence of a keto group directly attached to the alkyne. This process involves oxidation of one of the alkyne carbons into C2 of a 2-R-4,5-dihydroimidazole with the concomitant reduction of the other carbon to a methyl group. The sequence of Sonogashira coupling with the ethylenediamine-mediated fragmentation described in this work can be used for selective formal substitution of halogen in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.
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Scheiner, Steve. "Versatility of the Cyano Group in Intermolecular Interactions." Molecules 25, no. 19 (September 30, 2020): 4495. http://dx.doi.org/10.3390/molecules25194495.

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Several cyano groups are added to an alkane, alkene, and alkyne group so as to construct a Lewis acid molecule with a positive region of electrostatic potential in the area adjoining these substituents. Although each individual cyano group produces only a weak π-hole, when two or more such groups are properly situated, they can pool their π-holes into one much more intense positive region that is located midway between them. A NH3 base is attracted to this site, where it forms a strong noncovalent bond to the Lewis acid, amounting to as much as 13.6 kcal/mol. The precise nature of the bonding varies a bit from one complex to the next but typically contains a tetrel bond to the C atoms of the cyano groups or the C atoms of the linkage connecting the C≡N substituents. The placement of the cyano groups on a cyclic system like cyclopropane or cyclobutane has a mild weakening effect upon the binding. Although F is comparable to C≡N in terms of electron-withdrawing power, the replacement of cyano by F substituents substantially weakens the binding with NH3.
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Vohradská, Nikoleta, Esther M. Sánchez-Carnerero, Tomáš Pastierik, Ctibor Mazal, and Petr Klán. "Controlled photorelease of alkynoic acids and their decarboxylative deprotection for copper-catalyzed azide/alkyne cycloaddition." Chemical Communications 54, no. 44 (2018): 5558–61. http://dx.doi.org/10.1039/c8cc03341b.

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A controlled photorelease of alkynoic acids from a photoremovable protecting group (PPG) facilitates their subsequent decarboxylation to deliver terminal alkynes for a CuI-catalyzed azide/alkyne cycloaddition.
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Hadlington, Terrance J., Markus Hermann, Gernot Frenking, and Cameron Jones. "Two-coordinate group 14 element(ii) hydrides as reagents for the facile, and sometimes reversible, hydrogermylation/hydrostannylation of unactivated alkenes and alkynes." Chemical Science 6, no. 12 (2015): 7249–57. http://dx.doi.org/10.1039/c5sc03376d.

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The ambient temperature hydrometallations of a variety of unactivated alkene and alkyne substrates using two-coordinate hydrido-tetrylenes, :E(H)(L†) (E = Ge or Sn; L† = extremely bulky amide), are reported.
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Dissertations / Theses on the topic "Alkyne group"

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Harding, David James. "Redox-active group 6 transition metal alkyne complexes." Thesis, University of Bristol, 2000. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.324328.

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Boonyuen, Supakorn. "The redox chemistry of Group 6 metal alkyne complexes." Thesis, University of Bristol, 2005. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.420906.

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Humphrey, James Stuart. "Group 15 and alkyne derivatives of HR₄CO₁₂BH₂." Thesis, University of Cambridge, 1995. https://www.repository.cam.ac.uk/handle/1810/273012.

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Elser, Iris [Verfasser], and Michael R. [Akademischer Betreuer] Buchmeiser. "(Pre-)ionic and/or chiral alkene and alkyne metathesis catalysts of group 6 / Iris Elser ; Betreuer: Michael R. Buchmeiser." Stuttgart : Universitätsbibliothek der Universität Stuttgart, 2018. http://d-nb.info/1183678274/34.

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Bartlett, Ian Mark. "The redox activiation of alkyne ligands in group 6 transition metal complexes." Thesis, University of Bristol, 1997. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.390376.

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Fauché, Kévin. "NHC portant des azotures : intermédiaires dans la synthèse catalysée d‘hétérocycles polyazotés et auto-fonctionnalisation de complexes métal-NHC." Thesis, Université Clermont Auvergne‎ (2017-2020), 2018. http://www.theses.fr/2018CLFAC062/document.

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Les carbènes N-hétérocycliques (NHC) sont très utilisés pour complexer les métaux de transition. Ils quittent rarement ce rôle de ligand ancillaire et trouvent, depuis une vingtaine d’années, des applications en catalyse ou, plus récemment, en chimie médicinale. Dans ce travail, nous discuterons d’une méthode de synthèse douce conduisant à la formation de complexes AgI – NHC via une source d’argent soluble. Cette méthode nous a permis d’obtenir des complexes bien connus mais également d’accéder à une nouvelle série de complexes NHC-Ag-phosphine. Nous présenterons également une nouvelle réaction où des NHC portant une fonction azoture à proximité du carbone du carbène quittent leur rôle de ligand ancillaire et conduisent à la formation d’hétérocycles azotés par cyclisation carbène-nitrène. Cette réaction sera présentée en détail, ainsi que la caractérisation spectroscopique concernant une sous-série de composés fluorescents obtenus par cette méthode. Enfin, nous présenterons une stratégie de post-fonctionnalisation de complexes développée dans notre équipe. Des complexes argent(I)-NHC portant un azoture proches du centre carbénique catalysent leur propre fonctionnalisation. De plus, des complexes de cuivre(I) portant des azotures en position éloignée du centre métallique seront greffés sur des nanoparticules magnétiques pour servir de catalyseur recyclables
N-heterocyclic carbenes (NHC) are widely used to complex transition metals. They rarely leave their role as ancillary ligand and find, since 20 years, applications in catalysis or, more recently, in medicinal chemistry. In this work, we will discuss a mild synthetic method leading to the formation of AgI – NHC complexes via a soluble silver species. This method allowed us to obtain well known complexes but also to access a new series of NHC-Ag-phosphine complexes. We will also present a new reaction where NHC ligands bearing an azide function close to the carbenic center leave their role as ancillary ligand and lead to the formation of nitrogen rich heterocycles by a carbene-nitrene cyclization. This reaction will be presented in detail, along with the spectroscopic characterization regarding a sub-series of fluorescent compounds obtained by this method. Finally, we will present a post-functionalization strategy of complexes developed in our team. Silver(I)-NHC complexes tagged by an azide close to the carbenic center catalysed their own functionalization. Moreover, copper(I) complexes tagged by an azide function in a distant position from the metallic centre will be grafted on magnetic nanoparticles to act as recyclable catalysts
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Yahya, Rosiyah. "Alkane hydrogenolysis on supported Group VIII metals." Thesis, Brunel University, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.257670.

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Coles, Stuart Raymond. "Half-sandwich group 4 complexes in alkene polymerisation." Thesis, University of Warwick, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.439647.

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Bismuto, Alessandro. "Main group species for catalytic hydroboration." Thesis, University of Edinburgh, 2018. http://hdl.handle.net/1842/31537.

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Modern synthetic chemistry is unimaginable without transition metal catalysis. Yet the often high cost, toxicity and scarcity of many transition metals is driving attempts to find sustainable alternatives. Thus, the development of catalytic processes using main-group catalysts is now of broad interest. This thesis reports the development of a facile protocol for the aluminium-catalysed hydroboration of alkynes, alkenes and polar bonds using commercially-available catalysts. The catalytic hydroboration is proposed to occur by hydroalumination followed by product release through σ-bond metathesis with pinacol borane. An alternative route to alkenyl boranes is the 1,1-carboboration of alkynes using stoichiometric B(C6F5)3. A zwitterionic intermediate in the Piers' borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3 has been characterised and its divergent reactivity identified. This has led to the development of a B(C6F5)3 - catalysed hydroboration of alkynes using HBpin.
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Gustafson, Samantha Jane. "Computational Studies of Alkane C-H Functionalization by Main-Group Metals." BYU ScholarsArchive, 2016. https://scholarsarchive.byu.edu/etd/5992.

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The most efficient homogeneous catalysts for hydroxylation of light alkanes utilize transition metals in superacid solvent and operate by tandem electrophilic C-H activation/metal-alkyl (M-R) functionalization. An emerging alternative strategy to transition metals is the use of high-oxidation state main-group metals (e.g. TlIII, PbIV, IIII) that hydroxylate light alkanes. This dissertation reports density-functional theory calculations that reveal the mechanisms, reactivity, and selectivity of TlIII promoted alkane C-H functionalization in trifluoroacetic acid and TlIII-dialkyl functionalization in water. Calculations reveal that TlIII oxidizes alkanes via a closed-shell C-H activation and M-R functionalization mechanism that is similar to transition-metal C-H functionalization mechanisms. Comparison of TlIII to similar transition metals reveals that while TlIII and transition metals can have similar activation barriers for C-H activation, TlIII M-R functionalization is significantly faster due to a highly polar Tl-C bond and large TlIII/TlI reduction potential. The combination of a moderate C-H activation barrier combined with a low M-R functionalization barrier is critical to the success for TlIII promoted alkane C-H oxidation. The proposed TlIII C-H activation/M-R functionalization mechanism also provides an explanation for ethane conversion to a mixture of ethyl trifluoroacetate and ethane-1,2-diyl bis(2,2,2-trifluoroacetate). The reactivity of TlIII contrasts the lack of alkane oxidation by HgII. The C-H activation transition state and frontier-orbital interactions provide a straightforward explanation for the higher reactivity of TlIII versus HgII. This frontier-orbital model also provides a rationale for why the electron-withdrawing group in EtTFA provides "protection" against overoxidation. Calculations also reveal that TlIII-dialkyl functionalization by inorganic TlIII in water occurs by alkyl group transfer to form a TlIII-monoalkyl complex that is rapidly functionalized.
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Books on the topic "Alkyne group"

1

Yahya, Rosiyah. Alkane hydrogenolysis on supported group VIII metals. Uxbridge: Brunel University, 1990.

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Lancaster, Simon John. Cationic group IV metal alkyls as polymerisation catalysts. Norwich: University of East Anglia, 1992.

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Jaggar, Andrew J. The synthesis and reactions of cationic alkyl complexes of group (IV) transition metals. Norwich: University of East Anglia, 1992.

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Coffey, P. E. The synthesis and characterisation of hexa-alkoxy-substituted cyclotriphosphazenes with straight-chain alkyl groups of5 to 10 carbons long. Manchester: UMIST, 1994.

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Xu, Yao-Chang. Recations of group 6 transition metal carbene complexes: Alkylations, two-alkyne annulations, and applications to anthracyclinone syntheses. 1988.

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Benefiel, Annamarie. Kinetic and mechanistic studies of alkyl transfers from coordinated sulfur ligands of group VIII metal complexes. 1985.

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Chestakova, Alexandra. Interfacial equilibrium and dynamic properties of telechelic poly(ethylene oxide) end-capped by alkyl groups. 2003, 2003.

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Gwin, Janice L. Effect of ionizable surface groups on the adsorption of linear alkyl sulfates on polystyrene latex surfaces. 1988.

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Book chapters on the topic "Alkyne group"

1

Gooch, Jan W. "Alkyl Group." In Encyclopedic Dictionary of Polymers, 28. New York, NY: Springer New York, 2011. http://dx.doi.org/10.1007/978-1-4419-6247-8_447.

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Schurig, John E., Harry A. Meinema, Klaas Timmer, Byron H. Long, and Anna Maria Casazza. "Antitumor Activity of Bis[Bis(Diphenylphosphino)Alkane and Alkene] Group VIII Metal Complexes." In Ruthenium and Other Non-Platinum Metal Complexes in Cancer Chemotherapy, 205–16. Berlin, Heidelberg: Springer Berlin Heidelberg, 1989. http://dx.doi.org/10.1007/978-3-642-74760-1_9.

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Tsurugi, Hayato. "Group 4 Metal Alkyne, Alkene, and Allyl Complexes." In Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. Elsevier, 2021. http://dx.doi.org/10.1016/b978-0-12-820206-7.00038-x.

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Taber, Douglass. "New Methods for Functional Group Conversion." In Organic Synthesis. Oxford University Press, 2011. http://dx.doi.org/10.1093/oso/9780199764549.003.0010.

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Ilya M. Lyapkalo of the Academy of Sciences of the Czech Republic, Prague, showed (Synlett 2009, 558) that a ketone 1 reacted with the inexpensive nonafluorobutanesulfonyl fluoride in the presence of a phosphazene base to give first the enol sulfonate, and then the alkyne 2. The method worked well for aldehydes also. Christophe Darcel of the Université de Rennes I developed (Adv. Synth. Cat. 2009, 351, 367) an inexpensive Fe catalyst for the hydration of a terminal alkyne 3 to the ketone 4. Carlos Alonso-Moreno and Antonio Otero of the Universidad de Castilla-La Mancha devised (Adv. Synth. Cat. 2009, 351, 881) a Rh catalyst for the complementary hydration of a terminal alkyne 5 to the aldehyde, by way of the imine 7. Internal alkynes often give mixtures of ketones on hydration, but Bo Xu and Gerald B. Hammond of the University of Louisville found (J. Org. Chem. 2009, 74, 1640) a gold catalyst that converted an alkynyl ester 8 into the γ-keto ester 9. Jonathan M. J. Williams of the University of Bath developed (J. Am. Chem. Soc. 2009, 131, 1766; Tetrahedron Lett. 2009, 50, 3374) a Ru-catalyzed protocol for the alkylation of an amine 11 with an alcohol 10 . The reaction proceeded by oxi dation of the alcohol to the aldehyde, imine formation, and reduction using the hydride generated by the initial oxidation. José Luis García Ruano of the Universidad Autónoma de Madrid uncovered (Chem. Commun. 2009, 404) a similar conversion mediated by Raney Ni. There has been a great deal of work recently on the preparation and reaction of amides. Susumu Saito of Nagoya University prepared (J. Am. Chem. Soc. 2009, 131, 8748) a diaryl boronic acid that catalyzed the methanolysis of an imide 13 to the methyl ester 14 and the oxazolidinone 15. Jaume Vilarrasa of the Universitat de Barcelona reported (J. Org. Chem. 2009, 74, 2203) the catalyzed condensation of an acid 16 with an azide 17 to give the amide 18 . Both aryl and aliphatic azides participated in the reaction, and the enantiomeric integrity of the amide was maintained.
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Taber, Douglass F. "Organic Functional Group Interconversion." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0003.

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Alois Fürstner of the Max-Planck-Institut Mülheim devised (Angew. Chem. Int. Ed. 2013, 52, 14050) a Ru catalyst for the trans- selective hydroboration of an alkyne 1 to 2. Qingbin Liu of Hebei Normal University and Chanjuan Xi of Tsinghua University coupled (Org. Lett. 2013, 15, 5174) the alkenyl zirconocene derived from 3 with an acyl azide to give the amide 4. Chulbom Lee of Seoul National University used (Angew. Chem. Int. Ed. 2013, 52, 10023) a Rh catalyst to convert a terminal alkyne 5 to the ester 6. Laura L. Anderson of the University of Illinois, Chicago devised (Org. Lett. 2013, 15, 4830) a protocol for the conversion of a ter­minal alkyne 7 to the α-amino aldehyde 9. Dewen Dong of the Changchun Institute of Applied Chemistry developed (J. Org. Chem. 2013, 78, 11956) conditions for the monohydrolysis of a bis nitrile 10 to the monoamide 11. Aiwen Lei of Wuhan University optimized (Chem. Commun. 2013, 49, 7923) a Ni catalyst for the conversion of the alkene 12 to the enamide 13. Kazushi Mashima of Osaka University optimized (Adv. Synth. Catal. 2013, 355, 3391) a boronic ester catalyst for the conversion of an amide 14 to the ester 15. Jean- François Paquin of the Université Laval prepared (Eur. J. Org. Chem. 2013, 4325) the amide 17 by coupling an amine with the activated intermediate from reaction of an acid 16 with Xtal- Fluor E. Steven Fletcher of the University of Maryland School of Pharmacy designed (Tetrahedron Lett. 2013, 54, 4624) the azodicarbonyl dimorpholide 18 as a reagent for the Mitsunobu coupling of 19 with 20. The reduced form of 18 was readily separated by extraction into water and reoxidized. Jens Deutsch of the Universität Rostock found (Chem. Eur. J. 2013, 19, 17702) simple ligands for the Ru-mediated borrowed hydro­gen conversion of an alcohol 22 to the amine 23. Ronald T. Raines of the University of Wisconsin devised (J. Am. Chem. Soc. 2013, 135, 14936) a phosphinoester for the efficient conversion in water of an azide 24 to the diazo 25.
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Taber, Douglass F. "Organic Functional Group Interconversion." In Organic Synthesis. Oxford University Press, 2017. http://dx.doi.org/10.1093/oso/9780190646165.003.0004.

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Gojko Lalic of the University of Washington developed (Angew. Chem. Int. Ed. 2014, 53, 6473) conditions for the preparation of the fluoride 2 by SN2 displacement of the triflate 1. Ross M. Denton of the University of Nottingham showed (Tetrahedron Lett. 2014, 55, 799) that a polymer-bound phosphine oxide activated with oxalyl bromide would convert an alcohol 3 to the bromide 4. The polymer could be filtered off and reactivated directly. Jonas C. Peters and Gregory C. Fu of Caltech devised (J. Am. Chem. Soc. 2014, 136, 2162) a photochemically-activated Cu catalyst that mediated the displacement of the bromide 5 by the amide 6 to give 7. Mark L. Trudell of the University of New Orleans used (Synthesis 2014, 46, 230) an Ir catalyst to couple the amide 9 with the alcohol 8, leading to 10. Tohru Fukuyama of Nagoya University converted (Org. Lett. 2014, 16, 727) the unsaturated aldehyde 11 into the ester 12. As the transformation proceeded via proton­ation of the enolized acyl cyanide, the less stable diastereomer was formed kinetically. Brindaban C. Ranu of the Indian Association for the Cultivation of Science developed (Org. Lett. 2014, 16, 1040) conditions for the coupling of an alkenyl halide 13 with a phenol, leading to the vinyl ether 14. Inter alia, this would be a convenient way to hydrolyze an alkenyl halide to the aldehyde. Vinyl ethers can also be oxidized directly to the ester, and to the unsaturated aldehyde. Pallavi Sharma and John E. Moses of the University of Lincoln observed (Org. Lett. 2014, 16, 2158) that the cyanation of the alkenyl halide 15 delivered 16, with retention of the geometry of the alkene. Jitendra K. Bera of the Indian Institute of Technology Kanpur uncovered (Tetrahedron Lett. 2014, 55, 1444) “on water” conditions for the hydrolysis of a terminal alkyne 17 to the methyl ketone 18. Jiannan Xiang and Weimin He of Hunan University prepared (Eur. J. Org. Chem. 2014, 2668) the keto phosphonate 20 by hydrolysis of the alkynyl phosphonate 19. Ken-ichi Fujita of the National Institute of Advanced Industrial Science and Technology cyclized (Tetrahedron Lett. 2014, 55, 3013) the alkyne 21 with CO₂, leading to 22.
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Taber, Douglass F. "Functional Group Transformation: The Castle Synthesis of Celogentin C." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0004.

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Mark Cushman of Purdue University found (J. Org. Chem. 2010, 75, 3507) that a benzylic methyl ether 1 could be converted to the aldehyde 2 by N -bromosuccinimide. Two equivalents of NBS gave the methyl ester. Ning Jiao of Peking University used (Organic Lett. 2010, 12, 2888) NaN3 followed by DDQ to oxidize a benzylic halide 3 to the nitrile 4. Hugues Miel of Almac Sciences oxidized (Tetrahedron Lett. 2010, 51, 3216) the ketone 5 to the nitro derivative 6. The oxidative conversion of the nitro compound 7 to the ketone 8 described (Tetrahedron Lett. 2009, 50, 6389) by Vera L. Patrocinio Pereira of the Universidade Federal do Rio de Janeiro proceeded without epimerization. Sundarababu Baskaran of the Indian Institute of Technology Madras established (Angew. Chem. Int. Ed. 2010, 49, 804) that oxidative cleavage of the benzylidene acetal 9 delivered 10 with high regioselectivity. The intramolecular alkene dihydroxylation of 11 originated (Angew. Chem. Int. Ed. 2010, 49, 4491) by Erik J. Alexanian of the University of North Carolina gave 12 with high diastereocontrol. Ruimao Hua of Tsinghua University took advantage (J. Org. Chem. 2010, 75, 2966) of the H-donor properties of DMF to develop an efficient reduction of the alkyne 13 to the alkyne 14 . Alejandro F. Barrero of the University of Granada developed (J. Am. Chem. Soc. 2010, 132, 254) Ti (III) conditions for the reduction of the allylic alcohol 15 to the terminal alkene 16. Isolated alkenes were stable to these conditions. P. Veeraraghavan Ramachandran, also of Purdue University, effected (Tetrahedron Lett. 2010, 51, 3167) reductive amination of 17 to 18 using the now readily available NH3 - BH3 . Bin Ma and Wen-Cherng Lee of BiogenIdec developed (Tetrahedron Lett. 2010, 51, 385) a simple protocol for the conversion of an acid 19 to the free amine 20. Marc Lemaire of Université Lyons 1 established (Tetrahedron Lett. 2010, 51, 2092) that the silane 22 reduced primary, secondary, and tertiary amides to the aldehydes.
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8

Taber, Douglass F. "Functional Group Transformations." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0003.

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Mark Gandelman of the Technion–Israel Institute of Technology devised (Adv. Synth. Catal. 2011, 353, 1438) a protocol for the decarboxylative conversion of an acid 1 to the iodide 3. Doug E. Frantz of the University of Texas, San Antonio effected (Angew. Chem. Int. Ed. 2011, 50, 6128) conversion of a β-keto ester 4 to the diene 5 by way of the vinyl triflate. Pei Nian Liu of the East China University of Science and Technology and Chak Po Lau of the Hong Kong Polytechnic University (Adv. Synth. Catal. 2011, 353, 275) and Robert G. Bergman and Kenneth N. Raymond of the University of California, Berkeley (J. Am. Chem. Soc. 2011, 133, 11964) described new Ru catalysts for the isomerization of an allylic alcohol 6 to the ketone 7. Xiaodong Shi of West Virginia University optimized (Adv. Synth. Catal. 2011, 353, 2584) a gold catalyst for the rearrangement of a propargylic ester 8 to the enone 9. Xue-Yuan Liu of Lanzhou University used (Adv. Synth. Catal. 2011, 353, 3157) a Cu catalyst to add the chloramine 11 to the alkyne 10 to give 12. Kasi Pitchumani of Madurai Kamaraj University converted (Org. Lett. 2011, 13, 5728) the alkyne 13 into the α-amino amide 15 by reaction with the nitrone 14. Katsuhiko Tomooka of Kyushu University effected (J. Am. Chem. Soc. 2011, 133, 20712) hydrosilylation of the propargylic ether 16 to the alcohol 17. Matthew J. Cook of Queen’s University Belfast (Chem. Commun. 2011, 47, 11104) and Anna M. Costa and Jaume Vilarrasa of the Universitat de Barcelona (Org. Lett. 2011, 13, 4934) improved the conversion of an alkenyl silane 18 to the iodide 19. Vinay Girijavallabhan of Merck/Kenilworth developed (J. Org. Chem. 2011, 76, 6442) a Co catalyst for the Markovnikov addition of sulfide to an alkene 20. Hojat Veisi of Payame Noor University oxidized (Synlett 2011, 2315) the thiol 22 directly to the sulfonyl chloride 23. Nicholas M. Leonard of Abbott Laboratories prepared (J. Org. Chem. 2011, 76, 9169) the chromatography-stable O-Su ester 25 from the corresponding acid 24.
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Taber, Douglass F. "The Funk Synthesis of (-)-Nakadomarin A." In Organic Synthesis. Oxford University Press, 2013. http://dx.doi.org/10.1093/oso/9780199965724.003.0101.

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The Z alkene of nakadomarin A 3 suggested to Raymond L. Funk an approach (Org. Lett. 2010, 12, 4912) based on ring-closing alkyne metathesis. The efficient assembly of 3 he reported illustrates the power of convergent design in target-directed synthesis. A practical limit on applications of alkyne metathesis is the requirement for internal alkynes, necessitating methyl capping of a terminal alkyne. In an alternative approach, Professor Funk took advantage of the long-known ( J. Chem. Soc. 1954 , 3201) equilibration of a terminal alkyne 4 to the internal alkyne 5. Homologation of 5 with the phosphonate 6, followed by condensation with the ketone 7, then delivered the furan 8. The assembly of the other half of 1 began with the commercial alcohol derived by reduction of D -pyroglutamic acid. Protection gave 9, which on hydride addition and dehydration was converted to 10. One-carbon homologation with the Vilsmeier-Haack reagent proceeded with the expected regiocontrol. This set the stage for the triply convergent assembly of 14 , first reductive amination of the aldehyde 11 with 12 , then acylation of the resulting secondary amine with 13. The nucleophilic 14 was condensed with the aldehyde 8 to give an enone (not illustrated). Exposure of the enone to InCl 3 initiated an elegant cascade cyclization, first of the enamide in a conjugate sense to the enone, then Friedel-Crafts addition of the resulting N-stabilized carbocation to the furan, to deliver 15. The pendant silyloxymethyl group exerted the hoped-for diastereocontrol, allowing the direct construction of the central tetracycle of 3. Hydrolysis and decarboxylation completed the assembly of the diyne 1. Initially, it was found that exposure of 1 to a molybdenum catalyst delivered 2 in only modest yield. As an alternative, they employed the technically more challenging tungsten-based Schrock catalyst. Later, they found that the recently developed Fürstner Mo protocol also worked well. The amide 2 could readily be carried on to the triene 18. With the first-generation Grubbs catalyst G1, kinetic ring-closing metathesis of 18, to complete the assembly of (-)-nakadomarin 3, could be effected without jeopardizing the existing Z alkene.
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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 5 to 6 could be effected by exposure to TMNO. Stefan Bräse of the Karlsruhe Institute of Technology and Irina A. Balova of Saint Petersburg State University showed (J. Org. Chem. 2015, 80, 5546) that the bend of the Co complex of 7 enabled ring-closing metathesis, leading after deprotection to 8. Morten Meldal of the University of Copenhagen devised (Eur. J. Org. Chem. 2015, 1433) 9, the base-labile protected form of the aldehyde 10. Nicholas Gathergood of Dublin City University and Stephen J. Connon of the University of Dublin developed (Eur. J. Org. Chem. 2015, 188) an imidazolium catalyst for the exchange deprotection of 11 to 13, with the inexpensive aldehyde 12 as the acceptor. Peter J. Lindsay-Scott of Eli Lilly demonstrated (Org. Lett. 2015, 17, 476) that on exposure to KF, the isoxa­zole 14 unraveled to the nitrile 15. Masato Kitamura of Nagoya University observed (Tetrahedron 2015, 71, 6559) that the allyl ester of 16 could be removed to give 17, with the other alkene not affected. Benzyl ethers are among the most common of alcohol protecting groups. Yongxiang Liu and Maosheng Cheng of Shenyang Pharmaceutical University showed (Adv. Synth. Catal. 2015, 357, 1029) that 18 could be converted to 19 simply by expo­sure to benzyl alcohol in the presence of a gold catalyst. Reko Leino of Åbo Akademi University developed (Synthesis 2015, 47, 1749) an iron catalyst for the reductive benzylation of 20 to 21. Related results (not illustrated) were reported (Org. Lett. 2015, 17, 1778) by Chae S. Yi of Marquette University.
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Conference papers on the topic "Alkyne group"

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Silva, Victor Hugo Malamace da, and Glaucio Braga Ferreira. "Chemical interaction study between xanthate ligand and lead (II) using NBO, EDA and QTAIM analysis." In VIII Simpósio de Estrutura Eletrônica e Dinâmica Molecular. Universidade de Brasília, 2020. http://dx.doi.org/10.21826/viiiseedmol2020159.

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As a useful flotation agent, the xanthate ligand, O-alkyldithiocarbonates, has been used by different countries by its easy and inexpensive synthesis. More recently papers explored many different applications using this ligand within a complex of several metals cation. In order to study the proprieties of the lead (II) complex with such ligand, the object of this work is to provide a better understanding of the Pb-S bond using different theoretical approaches as NBO, EDA and QTAIM analysis and the influence caused by the different alkyl groups of the ligand. By an optimized structure, the NBO showed that the Pb-S is mainly composed by p orbital of the lead and by the p lone pair of the sulfur atom. The calculation with different alkyl groups highlights that the presence of a larger hydrocarbon chain provides a higher contribution of the s orbital of the lead atom to the interaction. Through the EDA analysis, the interaction between ligand and metal has the predominance of an electrostatic character. The size of the alkyl group has an impact on the value of both covalent and electrostatic character, making the interaction more covalent, due to a higher presence of an electronic density on sulfur atom. This density can be evaluated by the topological study of the QTAIM analysis, which enhances the fact that the charge over the sulfur atom gets higher when using a larger alkyl group for the xanthate ligand.
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Perez, Carlos, Stephen M. Walton, and Margaret S. Wooldridge. "An Experimental Investigation of the Effects of Functional Group Structure on Particulate Matter and NO Emissions of Oxygenated Hydrocarbons." In ASME 2007 International Mechanical Engineering Congress and Exposition. ASMEDC, 2007. http://dx.doi.org/10.1115/imece2007-41947.

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The effects of alkyl group size on nitric oxide and soot emissions in small esters was investigated using a multi-element diffusion burner (a Hencken burner) and pool fires at atmospheric pressure. The esters were chosen to examine chemical structure characteristics, e.g. carboxylic acid length, while holding other parameters constant (molecular weight, and C:H:O ratio), to determine the effects of various structural parameters on the particulate matter and NO emissions. The esters were chosen to vary alkyl chain length from one to four carbons in both their alcohol and carboxylic acid groups with the largest ester chosen containing 5 carbons in total. Increasing the carbon content increased the relative sooting tendencies of the esters. Within the isomer pairs considered, the sooting tendency was higher for compounds with longer alcohol groups compared to longer carboxylic groups. Although the NO results were convolved with temperature and structural effects are not isolated, the NO emissions were significantly affected by the addition of the esters to a baseline methane flame.
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Thorley, Karl J., Micai Benford, Yang Song, Sean R. Parkin, Chad Risko, and John E. Anthony. "Group 14 effects in alkynyl acene small molecule semiconductors." In 2021 IEEE International Flexible Electronics Technology Conference (IFETC). IEEE, 2021. http://dx.doi.org/10.1109/ifetc49530.2021.9580518.

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Carr, Matthew A., Patrick A. Caton, Leonard J. Hamilton, Jim S. Cowart, Marco Mehl, and William J. Pitz. "An Experimental and Modeling-Based Study Into the Ignition Delay Characteristics of Diesel Surrogate Binary Blend Fuels." In ASME 2011 Internal Combustion Engine Division Fall Technical Conference. ASMEDC, 2011. http://dx.doi.org/10.1115/icef2011-60027.

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This study examines the combustion characteristics of a binary mixture surrogate for possible future diesel fuels using both a single-cylinder research engine and a homogeneous reactor model using detailed chemical reaction kinetics. Binary mixtures of a normal straight-chain alkane (pure n-hexadecane, also known as n-cetane, C16H34) and an alkyl aromatic (toluene, C7H8) were tested in a single-cylinder research engine. Pure n-hexadecane was tested as a baseline reference, followed by 50%, 70%, and 80% toluene in hexadecane blends. Testing was conducted at fixed engine speed and constant indicated load. As references, two conventional petroleum-based fuels (commercial diesel and US Navy JP-5 jet fuel) and five synthetic Fischer-Tropsch-based fuels were also tested. The ignition delay of the binary mixture surrogate increased with increasing toluene fraction and ranged from approximately 1.3 ms (pure hexadecane) to 3.0 ms (80% toluene in hexadecane). While ignition delay changed substantially, the location of 50% mass fraction burned did not change as significantly due to a simultaneous change in the premixed combustion fraction. Detailed chemical reaction rate modeling using a constant pressure, adiabatic, homogeneous reactor model predicts a chemical ignition delay with a similar trend to the experimental results, but shorter overall magnitude. The difference between this predicted homogeneous chemical ignition delay and the experimentally observed ignition delay is defined as the physical ignition delay due to processes such as spray formation, entrainment, mixing, and vaporization. On a relative basis, the addition of 70% toluene to hexadecane causes a nearly identical relative increase in both physical and chemical ignition delay of approximately 50%. The chemical kinetic model predicts that, even though the addition of toluene delays the global onset of ignition, the initial production of reactive precursors such as HO2 and H2O2 may be faster with toluene due to the weakly bound methyl group. However, this initial production is insufficient to lead to wide-scale chain branching and ignition. The model predicts that the straight-chain alkane component (hexadecane) ignites first, causing the aromatic component to be consumed shortly thereafter. Greater ignition delay observed with the high toluene fraction blends is due to consumption of OH radicals by toluene. Overall, the detailed kinetic model captures the experimentally observed trends well and may be able to provide insight as to the relationship between bulk properties and physical ignition delay.
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Bialecka-Florjanczyk, Ewa, E. Kowalczyk, Joanna Soltysiak, and Jan Przedmojski. "Liquid crystalline cyclic oligosiloxanes containing long alkyl substituents as an end group." In SPIE Proceedings, edited by Jozef Zmija. SPIE, 2004. http://dx.doi.org/10.1117/12.581067.

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Vasilyeva, Svetlana V., Dmitrii A. Konevetz, and Vladimir N. Silnikov. "Synthesis of novel nucleoside derivatives containing precursor alkyne or amino groups for the post-synthetic functionalisation of nucleic acids." In XVth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2011. http://dx.doi.org/10.1135/css201112130.

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Van Reempts, J., B. Van Deuren, M. Borqers, and F. De Clerck. "R 68 070, A COMBINED TXA2-SYNTHETASE/TXA2-PROSTAGLANDIN ENDOPEROXIDE RECEPTOR INHIBITOR. REDUCES CEREBRAL INFARCT SIZE AFTER PHOTOCHEMICALLY INITIATED THROMBOSIS IN SPONTANEOUSLY HYPERTENSIVE RATS." In XIth International Congress on Thrombosis and Haemostasis. Schattauer GmbH, 1987. http://dx.doi.org/10.1055/s-0038-1643470.

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The effects of R 68 070, an oxime-alkane carboxylic acid derivative combining specific thromboxane A2 (TXA2) synthetase inhibition with TXA2/prostaglandin endoperoxide receptor blockade in one molecule, were investigated in a model of photochemically induced stroke in spontaneously hypertensive rats.Each experimental group was compared with an untreated control group. All animals were anesthetized with halothane in N20/02 and artificially ventilated. After incision of the scalp and stereotaxic positioning of a fibre optic light source, halothane was discontinued. When physiological variables reached normal values, a focal cortical infarction was produced by injection of 10 mg.kg-1 rose bengal and 20 min irradiation of the brain through the intact skull. Four hours later the brains were perfusion fixed and damaged areas measured on consecutive histologic sections. Infarct size was calculated by numerical integration.R 68 070 (40 mg.kg-1 p.o.,-3 h) significantly reduced the cerebral infarct size to 2.32 mm3 compared with 5.78 mm3 in controls (median values; n = 5; p < 0.05). At 2.5 mg.kg-1 the lesion was reduced from 11.75 mm3 in the control group to 7.82 mm3 in the treated group (n = 5; p = 0.095). Serum TXB2 levels were reduced by > 80 %.Production of damage in this model is based upon photodynamic generation of singlet molecular oxygen, resulting in peroxidative endothelial cell injury and subsequent platelet thrombus formation. Protection with R 68 070 can be explained by the anti-thrombotic effect of the compound. The relative contribution to this protective effect of synthetase and receptor blockade by R 68 070 are being investigated.
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Ford, M. J., R. C. Hoft, J. D. Gale, and A. M. Mcdonagh. "A new class of self-assembled monolayers on gold using an alkynyl group as a linker." In 2006 International Conference on Nanoscience and Nanotechnology. IEEE, 2006. http://dx.doi.org/10.1109/iconn.2006.340700.

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Honsho, Kazuhiro, Hirokazu Terai, Hiroshi Yamazoe, Toshiaki Tatsuta, and Osamu Tsuji. "New Plasma Surface Treatment for Wire Bonding Process -Effect of Sublimation with Alkyl Group Radicals-." In 2001 International Conference on Solid State Devices and Materials. The Japan Society of Applied Physics, 2001. http://dx.doi.org/10.7567/ssdm.2001.b-1-5.

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Kockmann, Norbert, and Dominique M. Roberge. "Liquid-Liquid Test Reactions to Characterize 2-Phase-Mixing in Microchannels." In ASME 2011 9th International Conference on Nanochannels, Microchannels, and Minichannels. ASMEDC, 2011. http://dx.doi.org/10.1115/icnmm2011-58157.

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Multiphase flow is often found in chemical engineering, food processing, or analytics. First contacting and droplet generation as well as coalescence and re-dispersion have high importance for the flow characteristics. In all processes, the channel geometry, fluid properties, and flow velocity determine the flow regime, droplet size, and interfacial area. The hydrolysis of alkyl acetates in organic phase with sodium hydroxide NaOH in the aqueous phase is investigated as flexible test reaction for mass transfer and interfacial area. For right design of the characteristic time for mass transfer, the alkyl group is chosen from ethyl, isopropyl or n-butyl, which differ in water solubility, diffusivity and rate constant. The consumption of NaOH is used for calculation of specific area and related mass transfer coefficient. Different channel geometries are characterized and design considerations are conducted.
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Reports on the topic "Alkyne group"

1

Weinberg, W. H. (The activation and decomposition of alkanes on group VIII transition metal surfaces: Dynamics, kinetics and spectroscopy). Office of Scientific and Technical Information (OSTI), January 1990. http://dx.doi.org/10.2172/5730531.

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Weinberg, W. H. [The activation and decomposition of alkanes on group VIII transition metal surfaces: Dynamics, kinetics and spectroscopy]. Progress report. Office of Scientific and Technical Information (OSTI), December 1990. http://dx.doi.org/10.2172/10128607.

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3

Lampland, Nicole Lynn. Beyond alkyl transfer: Synthesis of main group metal (Mg, Ca, Zn) silyl and tris(oxazolinyl)borato complexes and their stoichiometric and catalytic reactions with borane Lewis acids and carbonyls. Office of Scientific and Technical Information (OSTI), May 2015. http://dx.doi.org/10.2172/1417988.

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4

Percec, V., Q. Zheng, and M. Lee. Molecular Engineering of Liquid Crystal Polymers by Living Polymerization. 13. Synthesis and Living Cationic Polymerization of 4-((S(-)-2- Methyl-1-Butyl)Oxycarbonyl)-4'-(omega-Oxyalkyl-1-Vinyl Ether)Biphenyl with Undecanyl and Hexyl Alkyl Groups. Fort Belvoir, VA: Defense Technical Information Center, April 1991. http://dx.doi.org/10.21236/ada235791.

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