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Pure Appl. Chem., 1980, Vol. 52, No. 4, pp. 771-788

http://dx.doi.org/10.1351/pac198052040771

Old and new ylid chemistry

H. J. Bestmann

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  • Byrne Peter A., Gilheany Declan G.: The modern interpretation of the Wittig reaction mechanism. Chem. Soc. Rev. 2013, 42, 6670. <http://dx.doi.org/10.1039/c3cs60105f>
  • Baccolini Graziano, Delpivo Camilla, Micheletti Gabriele: Wittig Reaction: Role of Steric Effects in Explaining the Prevalent Formation of Z Olefin from Nonstabilized Ylides. Phosphorus, Sulfur, and Silicon and the Related Elements 2012, 187, 1291. <http://dx.doi.org/10.1080/10426507.2012.694000>
  • Bestmann Hans Jürgen: Synthese von Heterocyclen unter Verwendung von Phosphoryliden. Bull Soc Chim Belges 2010, 90, 519. <http://dx.doi.org/10.1002/bscb.19810900602>
  • Broos René, Anteunis Marc J. O.: The reaction of benzyltriphenylarsonium ylides with aldehydes. A note about the mechanism of the wittig reaction. Bull Soc Chim Belges 2010, 97, 271. <http://dx.doi.org/10.1002/bscb.19880970406>
  • Buck Henk M.: Mechanistic aspects of organophosphorus chemistry. Recl Trav Chim Pays-Bas 2010, 100, 217. <http://dx.doi.org/10.1002/recl.19811000602>
  • Heimbach Paul, Bartik Tamas, Boese Roland, Schenkluhn Hartmut, Szczendzina Georg, Zeppenfeld Eva: Ordungsfaktoren in der organischen Synthese Mustererkennung als Methode der Faktorenanalyse. Z Chem 2010, 28, 121. <http://dx.doi.org/10.1002/zfch.19880280402>
  • Bandmann Heinz, Bartik Tamás, Bauckloh Sylvia, Behler Ansgar, Brille Frank, Heimbach Paul, Louven Johannes-Wilhelm, Ndalut Paulo, Preis Heinz-Günther, Zeppenfeld Eva: Untersuchungen im Wittig-System nach einem ordnenden Konzept auf der Basis alternativer Prinzipien. Z Chem 2010, 30, 193. <http://dx.doi.org/10.1002/zfch.19900300602>
  • McNulty James, Das Priyabrata: A Direct Synthesis of Vinylphosphonium Salts from α-Trimethylsilyl Ylides and Non-Enolizable Aldehydes. Chem Eur J 2008, 14, 8469. <http://dx.doi.org/10.1002/chem.200801358>
  • Schaumann Ernst, Ketcham Roger: [2+2]-Cycloreversionen. Angew Chem 2006, 94, 231. <http://dx.doi.org/10.1002/ange.19820940402>
  • Bestmann Hans Jürgen, Bomhard Andreas: Synthese trisubstituierter Olefine über trimethylsilylierte Phosphor-Ylide. Angew Chem 2006, 94, 562. <http://dx.doi.org/10.1002/ange.19820940736>
  • Bestmann Hans Jürgen, Schobert Rainer: Neue Synthese makrocyclischer Lactone. Angew Chem 2006, 95, 810. <http://dx.doi.org/10.1002/ange.19830951024>
  • Kalaiselvan Anbarasan, Venuvanalingam Ponnambalam: Oxaphosphetane versus betaine formation in epoxide ring opening by PPh3: a mechanistic probe by ab initio and DFT modeling. Tetrahetron Lett 2005, 46, 4087. <http://dx.doi.org/10.1016/j.tetlet.2005.04.024>
  • Pandolfi Enrique M., López Gloria V., Días Eduardo, Seoane Gustavo A.: Solvent Effect in the Wittig Reaction Under Boden's Conditions. Synth Common 2003, 33, 2187. <http://dx.doi.org/10.1081/SCC-120021496>
  • Nagaki Masahiko, Yamamoto Hiroto, Takahashi Ayumi, Maki Yuji, Ishibashi Junji, Nishino Tokuzo, Koyama Tanetoshi: Substrate specificity of thermostable farnesyl diphosphate synthase with respect to 4-alkyl group homologs of isopentenyl diphosphate. Mol Catal B Enzym 2002, 17, 81. <http://dx.doi.org/10.1016/S1381-1177(02)00012-7>
  • Renault Olivier, Dallemagne Patrick, Rault Sylvain: FRIEDEL-CRAFTS ACYLATION WITH MALONIC ACIDS IN POLYPHOSPHORIC ACID. Org Prep Proced Int 1999, 31, 324. <http://dx.doi.org/10.1080/00304949909458327>
  • Kawashima Takayuki, Soda Tomokazu, Okazaki Renji: N-apicale 1, 2λ5-Azaphosphetidine mit P-Pentakoordination und ihre N-äquatorialen Pseudorotamere. Angew Chem 1996, 108, 1206. <http://dx.doi.org/10.1002/ange.19961081024>
  • Hughes Karin A., Dopico Pablo G., Sabat Michal, Finn M. G.: TiIV-Komplexe mit Brücken-Ylidliganden: Verbindungen mit zwei oxophilen Zentren und Reaktionen mit Aldehyden. Angew Chem 1993, 105, 603. <http://dx.doi.org/10.1002/ange.19931050424>
  • Kawashima Takayuki, Kato Katsuhiro, Okazaki Renji: Synthese, Struktur und Thermolyse eines 3-Methoxycarbonyl-1,2λ5-oxaphosphetans. Angew Chem 1993, 105, 941. <http://dx.doi.org/10.1002/ange.19931050634>
  • Marí Frank, Lahti Paul M., McEwen William E.: Molecular modeling of the Wittig olefination reaction: Part 2: A molecular orbital approach at the MNDO-PM3 level. Heteroatom Chem 1991, 2, 265. <http://dx.doi.org/10.1002/hc.520020208>
  • Yamataka Hiroshi, Hanafusa Terukiyo, Nagase Shigeru, Kurakake Toshiya: Theoretical study on the transition state of oxaphosphetane formation between ethylidenetriphenylphosphorane and acetaldehyde. Heteroatom Chem 1991, 2, 465. <http://dx.doi.org/10.1002/hc.520020407>
  • Thilgen Carlo, Vögtle Fritz: Macrocyclic pyridinophanetetraene. Chem Ber 1990, 123, 2445. <http://dx.doi.org/10.1002/cber.19901231228>
  • Marí Frank, Lahti Paul M., McEwen William E.: Molecular modeling of oxaphosphetane intermediates of wittig olefination reactions. Heteroatom Chem 1990, 1, 255. <http://dx.doi.org/10.1002/hc.520010311>
  • Boubia B, Mioskowski C, Bellamy F: Stereospecific E olefination of aldehydes with a bisbenzylic arsonium ylid-anion. Tetrahetron Lett 1989, 30, 5263. <http://dx.doi.org/10.1016/S0040-4039(01)93758-X>
  • Le Bigot Yves, Delmas Michel, Gaset Antoine: Reactions en milieu heterogene solide-liquide faiblement hydrate : la reaction de wittig dans le systeme hydroxydes alcalins/solvant organique aprotique. Tetrahedron 1988, 44, 1057. <http://dx.doi.org/10.1016/S0040-4020(01)85886-5>
  • Soderquist John A., Anderson Charles L.: A highly stereoselective synthesis of Z-1,2-dialkylvinylsilanes from acylsilane/ylide chemistry. Tetrahetron Lett 1988, 29, 2425. <http://dx.doi.org/10.1016/S0040-4039(00)87898-3>
  • Webb Thomas H., Thomasco Lisa M., Schlachter Stephen T., Gaudino John J., Wilcox Craig S.: Insight into the unusual reactions of stabilized phosphorus ylides with lactols. A specific intramolecular hydroxyl group effect leads to high z-selectivity. Tetrahetron Lett 1988, 29, 6823. <http://dx.doi.org/10.1016/S0040-4039(00)88450-6>
  • Valverde Serafía, Martin-Lomas Manuel, Herradon Bernardo, Garcia-Ochoa Silvestre: The reaction of carbohydrate-derived alkoxyaldehydes with methoxycarbonylmethylenetriphenylphosphorane: stereoselective synthesis of β-unsaturated esters. Tetrahedron 1987, 43, 1895. <http://dx.doi.org/10.1016/S0040-4020(01)81502-7>
  • Bestmann Hans Jürgen, Ermann Peter, Rüppel Hartmann, Sperling Walter: Retinoide und Carotinoide, V. Synthese von modifizierten Retinalen. Liebigs Ann Chem 1986, 1986, 479. <http://dx.doi.org/10.1002/jlac.198619860307>
  • Streitwieser Andrew, McDowell Robert S.: Electron density analysis of the wittig reaction between methylenephosphorane and formaldehyde. Journal of Molecular Structure: THEOCHEM 1986, 138, 89. <http://dx.doi.org/10.1016/0166-1280(86)87010-5>
  • Bigot Yves Le, Delmas Michel, Gaset Antoine: Reactions en milieu heterogene solide-liquide faiblement hydrate II-la reaction de wittig dans les systemes carbonates alcalins/solvant organique aprotique. Tetrahedron 1986, 42, 339. <http://dx.doi.org/10.1016/S0040-4020(01)87435-4>
  • Le Bigot Y., Elgharbi R., Delmas M., Gaset A.: Reactions en milieu heterogene solide-liquide faiblement hydrate III. Tetrahedron 1986, 42, 3813. <http://dx.doi.org/10.1016/S0040-4020(01)87536-0>
  • Pietrusiewicz K. Michał, Monkiewicz Jarosław: Anionic activation of stabilized ylides. A highly Z-stereoselective wittig reaction of (3-ethoxycarbonyl-2-oxopropylidene)triphenyl-phosphorane with aliphatic aldehydes. Tetrahetron Lett 1986, 27, 739. <http://dx.doi.org/10.1016/S0040-4039(00)84088-5>
  • Bestmann Hans Jürgen, Arenz Thomas: Synthese deuterierter und brom-substituierter olefine aus dialkylboryl-alkylidentriphenylphosphoranen. Tetrahetron Lett 1986, 27, 1995. <http://dx.doi.org/10.1016/S0040-4039(00)84430-5>
  • Maryanoff Bruce E., Reitz Allen B.: DELVING INTO THE WITTIG REACTION-STEREOCHEMISTRY AND MECHANISM. STEREOCHEMICAL IDIOSYNCRASIES AND MECHANISTIC IMPLICATIONS1. Phosphorous and Sulfur and the Related Elements 1986, 27, 167. <http://dx.doi.org/10.1080/03086648608072769>
  • Bestmann Hans Jürgen, Schmidt Martin, Schobert Rainer: Kettenverlängernde Difunktionalisierung von Grignard-Verbindungen durch Umsetzung mit Ketenylidentriphenylphosphoran. Angew Chem 1985, 97, 418. <http://dx.doi.org/10.1002/ange.19850970522>
  • Bestmann Hans Jürgen, Schobert Rainer: Chemoselektive Mehrkomponenten-Synthese von α-β-ungesättigten Estern und Lactonen sowie deren Diels-Alder-Addukten. Angew Chem 1985, 97, 783. <http://dx.doi.org/10.1002/ange.19850970925>
  • Bestmann Hans Jürgen, Schmidt Martin, Schobert Rainer: Chain-Lengthening Difunctionalization of Grignard Compounds by Reaction with Ketenylidenetriphenylphosphorane. Angew Chem Int Ed Engl 1985, 24, 405. <http://dx.doi.org/10.1002/anie.198504051>
  • Bestmann Hans Jürgen, Schobert Rainer: Chemoselective Multicomponent Synthesis of α,β-Unsaturated Esters and Lactones and of Their Diels-Alder Adducts. Angew Chem Int Ed Engl 1985, 24, 790. <http://dx.doi.org/10.1002/anie.198507901>
  • Bestmann Hans Jürgen, Schade Gerold, Lütke Harry, Mönius Thomas: Kumulierte Ylide, XVII. Synthese von cyclischen Verbindungen aus Triphenyl[(phenylimino)ethenyliden]phosphoran und Oxocarbonsäuren – Eine neue Anellierungsmethodik. Chem Ber 1985, 118, 2640. <http://dx.doi.org/10.1002/cber.19851180708>
  • Seebach Dieter, Brook Michael A.: Reversed Stereochemical Course of theMichael Addition of Cyclohexanone to β-Nitrostyrenes by Using 1-(Trimethylsiloxy)cyclohexene/Dichloro(diisopropoxy)titanium. Preliminary Communication. HCA 1985, 68, 319. <http://dx.doi.org/10.1002/hlca.19850680205>
  • Hodge P., Khoshdel E.: Wittig syntheses of dihalo-olefins by reaction of carbonyl compounds with polymer-supported phosphines and carbon tetrahalides. Reactive Polymers, Ion Exchangers, Sorbents 1985, 3, 143. <http://dx.doi.org/10.1016/0167-6989(85)90056-X>
  • Pelter Andrew, Buss Dieter, Pitchford Andrew: The dimesitylboron group in organic synthesis 7. A unique variant of the Boron-Wittig reaction which stereoselectively yields 1,2-diols. Tetrahetron Lett 1985, 26, 5093. <http://dx.doi.org/10.1016/S0040-4039(01)80861-3>
  • Bestmann Hans Jürgen, Lütke Harry: Stereospezifischer aufbau ungesättigter macrocyclischer ketone. Tetrahetron Lett 1984, 25, 1707. <http://dx.doi.org/10.1016/S0040-4039(01)81150-3>
  • Bassindale Alan R., Ellis Richard J., Taylor Peter G.: The peterson reaction, part 1, the effect of reaction conditions and steric crowding. Tetrahetron Lett 1984, 25, 2705. <http://dx.doi.org/10.1016/S0040-4039(01)81268-5>
  • Husband James B., McNab Hamish: THE THERMOLYSIS OF PENTA-COORDINATE PHOSPHORUS HETEROCYCLES. Phosphorous and Sulfur and the Related Elements 1984, 20, 207. <http://dx.doi.org/10.1080/03086648408077630>
  • Bestmann Hans Jürgen, Schobert Rainer: A Novel Synthesis of Macrocyclic Lactones. Angew Chem Int Ed Engl 1983, 22, 780. <http://dx.doi.org/10.1002/anie.198307801>
  • Mulzer Johann, Lammer Ortrud: Olefins from β-Hydroxycarboxylic Acids - Synthesis of Isomerically Pure α- and β-Asarone. Angew Chem Int Ed Engl 1983, 22, 887. <http://dx.doi.org/10.1002/anie.198308870>
  • Bestmann Hans Jürgen, Ermann Peter: Reaktionen mit Phosphinalkylenen, 44. Eine weitere Synthese von (Z)-α,β-ungesättigten Aldehyden. Chem Ber 1983, 116, 3264. <http://dx.doi.org/10.1002/cber.19831160922>
  • Bigot Yves Le, Delmas Michel, Gaset Antoine: Reaction de wittig en milieu heterogene solide-liquide : transformation directe des aldehydes phenoliques naturels en alcenes. Tetrahetron Lett 1983, 24, 193. <http://dx.doi.org/10.1016/S0040-4039(00)81363-5>
  • Maryanoff Bruce E., Reitz Allen B., Duhl-Emswiler Barbara A.: Stereochemical observations on the Wittig reaction of oxido phosphonium ylides with aldehydes. Tetrahetron Lett 1983, 24, 2477. <http://dx.doi.org/10.1016/S0040-4039(00)81959-0>
  • Schaumann Ernst, Ketcham Roger: [2 + 2]-Cycloreversions. Angew Chem Int Ed Engl 1982, 21, 225. <http://dx.doi.org/10.1002/anie.198202253>
  • Bestmann Hans Jürgen, Bomhard Andreas: Synthesis of Trisubstituted Olefinsvia Trimethylsilylated Phosphorus Ylides. Angew Chem Int Ed Engl 1982, 21, 545. <http://dx.doi.org/10.1002/anie.198205451>
  • Bestmann Hans Jürgen, Roth Kurt, Ettlinger Manfred: Kumulierte Ylide, XII. Eine stereoselektive Synthesemethode für (Z)-α,β-ungesättigte Aldehyde2). Chem Ber 1982, 115, 161. <http://dx.doi.org/10.1002/cber.19821150116>
  • Kauffmann Thomas, Kriegesmann Reinhard, Hamsen Angelika: Neue Reagenzien, XXI. Stereospezifische Carbonylolefinierung wahlweise zumE- oderZ-Olefin durch Reagenzien mit Stannyl- oder Plumbyl-Abgangsgruppe. Chem Ber 1982, 115, 1818. <http://dx.doi.org/10.1002/cber.19821150515>
  • Kunze Udo, Merkel Reinhard, Winter Werner: Koordinationschemie funktioneller Phosphor-Ylide, IV. Kristallstruktur von 2-Methyl-2-(triphenylphosphonio)dithio-propionat und 3,5-Diisopropyliden-1,2,4-trithiolan. Zum Ablauf der Betain-Trithiolan-Umlagerung. Chem Ber 1982, 115, 3653. <http://dx.doi.org/10.1002/cber.19821151116>
  • Bestmann Hans Jürgen, Schmid Günter, Kisielowski Lothar: Synthesis of Three-Membered Rings by Means of Phosphorus Ylids. Isr. J. Chem. 1982, 22, 45. <http://dx.doi.org/10.1002/ijch.198200008>
  • Bestmann Hans Jürgen, Süβ Joachim: Eine neue stereoselektive Synthese des “Birnenesters” (2E,4Z)-2,4-Decadiensäure-ethylester. Liebigs Ann Chem 1982, 1982, 363. <http://dx.doi.org/10.1002/jlac.198219820219>
  • Bestmann Hans Jürgen, Koschatzky Karl Heinrich, Platz Hans, Süß Joachim, Vostrowsky Otto, Knauf Werner, Burghardt Gerhard, Schneider Isolde: Pheromone, XL. Stereoselektive Synthese des Pheromonkomplexes von Lasio-campidae-Arten (Lepidoptera); ein Sexuallockstoff für den KiefernspinnerDendrolimus pini. Liebigs Ann Chem 1982, 1982, 1359. <http://dx.doi.org/10.1002/jlac.198219820712>
  • Bestmann Hans Jürgen, Koschatzky Karl Heinrich, Vostrowsky Otto: Pheromone XLI. Stereoselektive Synthesen von 1,5- und 1,6-Alkadienen als Sexualpheromone und Pheromonanaloge. Liebigs Ann Chem 1982, 1982, 1478. <http://dx.doi.org/10.1002/jlac.198219820807>
  • Bestmann H. J., Vostrowsky O.: Insektenpheromone. Naturwiss 1982, 69, 457. <http://dx.doi.org/10.1007/BF00365811>
  • Godleski S.A., Heacock D.J., McKelvey J.M.: MNDO study of phosphine- and amine-substituted silicenium ions. Tetrahetron Lett 1982, 23, 4453. <http://dx.doi.org/10.1016/S0040-4039(00)85626-9>
  • Bigot Y. Le, Delmas M., Gaset A.: A Simplified Wittig Synthesis Using Solid/Liquid Transfer Processes : III‐ The use of a protic solvent for the preferential synthesis of E-alkenes. Synth Common 1982, 12, 1115. <http://dx.doi.org/10.1080/00397918208065978>
  • Bestmann Hans Jürgen, Saalfrank Rolf W.: Kumulierte Ylide, XI. Umsetzung von Isocyanaten und Isothiocyanaten mit (2,2-Diethoxyvinyliden)triphenylphosphoran. Chem Ber 1981, 114, 2661. <http://dx.doi.org/10.1002/cber.19811140731>
  • Seebach Dieter, Goliński Jerzy: Synthesis of Open-Chain 2,3-Disubstituted 4-nitroketones by DiastereoselectiveMichael-addition of (E)-Enamines to (E)-Nitroolefins. A topological rule for C, C-bond forming processes between prochiral centres. Preliminary communication. HCA 1981, 64, 1413. <http://dx.doi.org/10.1002/hlca.19810640518>
  • Bestmann Hans J¨rgen, Süß Joachim, Vostrowsky Otto: Pheromone XXXIV. Synthese konjugiert-ungesättigter Lepidopterenpheromone und Analoga. Liebigs Ann Chem 1981, 1981, 2117. <http://dx.doi.org/10.1002/jlac.198119811205>
  • Maryanoff Bruce E., Duhl-Emswiler Barbara A.: Trans stereoselectivity in the reaction of (4-carboxybutylidene)triphenylphosphorane with aromatic aldehydes. Tetrahetron Lett 1981, 22, 4185. <http://dx.doi.org/10.1016/S0040-4039(01)82099-2>
  • Plénat Françoise: Nouvelle synthese de sels d'alcadien-1,3 yl phosphonium. Tetrahetron Lett 1981, 22, 4705. <http://dx.doi.org/10.1016/S0040-4039(01)83018-5>