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Pure Appl. Chem., 1979, Vol. 51, No. 3, pp. 515-533

http://dx.doi.org/10.1351/pac197951030515

Synthesis of polyenes via phosphonium ylids

H. J. Bestmann

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  • 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>
  • Das Jhantu, Ghosh Somnath: A new synthesis of flavones and pyranoflavone by intramolecular photochemical Wittig reaction in water. Tetrahedron Letters 2011, 52, 7189. <http://dx.doi.org/10.1016/j.tetlet.2011.10.134>
  • Bestmann H. J., Saalbaum H.: Reactions with phosphinealkylenes XXXVII. : Reactions of phosphinealkylenes with Cos. A method for the formation of thiolesters. Bull Soc Chim Belges 2010, 88, 951. <http://dx.doi.org/10.1002/bscb.19790881116>
  • 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>
  • Schaumann Ernst, Ketcham Roger: [2+2]-Cycloreversionen. Angew Chem 2006, 94, 231. <http://dx.doi.org/10.1002/ange.19820940402>
  • Hafner Andreas, Bieri Jost H., Prewo Roland, Philipsborn Wolfgang Von, Salzer Albrecht: Metallorganische Varianten der Wittig-Reaktion: Synthese und Struktur von trans-μ(2-5 : 8-11-η-Dodecapentaen)-bis(tricarbonyleisen). Angew Chem 2006, 95, 736. <http://dx.doi.org/10.1002/ange.19830950912>
  • 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>
  • Dambacher Jesse, Zhao Wen, El-Batta Amer, Anness Robert, Jiang Changchun, Bergdahl Mikael: Water is an efficient medium for Wittig reactions employing stabilized ylides and aldehydes. Tetrahetron Lett 2005, 46, 4473. <http://dx.doi.org/10.1016/j.tetlet.2005.04.105>
  • Oh Joon Seok, Hyun Kim Byung, Gyu Kim Young: (E)-Selective Wittig reactions of Garner's aldehyde with nonstabilized ylides. Tetrahetron Lett 2004, 45, 3925. <http://dx.doi.org/10.1016/j.tetlet.2004.03.101>
  • Hwang Jiann-Jyh, Lin Ruey-Lih, Shieh Ruey-Lone, Jwo Jing-Jer: Study of the Wittig reaction of benzyltriphenylphosphonium salt and benzaldehyde via ylide-mediated phase-transfer catalysis. Journal of Molecular Catalysis A 1999, 142, 125. <http://dx.doi.org/10.1016/S1381-1169(98)00274-X>
  • Bestmann Hans Jürgen, Groß Andreas: Reaktionen von vinylketonen mit stabilisierten phosphoniumyliden. Tetrahetron Lett 1997, 38, 4765. <http://dx.doi.org/10.1016/S0040-4039(97)01043-5>
  • Sandri Jacqueline, Soto Thierry, Gras Jean-Louis, Viala Jacques: A convergent strategy toward linear cis-skipped polyenes. Tetrahetron Lett 1997, 38, 6611. <http://dx.doi.org/10.1016/S0040-4039(97)01524-4>
  • Haugan Jarle André, Liaaen-Jensen Synnøve: Total synthesis of acetylenic carotenoids. Tet Asymm 1994, 5, 1781. <http://dx.doi.org/10.1016/0957-4166(94)80087-1>
  • Cherkasov Rafael A, Pudovik Michael A: Heterophosphacyclanes in organic synthesis. RUSS CHEM REV 1994, 63, 1019. <http://dx.doi.org/10.1070/RC1994v063n12ABEH000132>
  • Janecki Tomasz: A Novel Route to Substituted Trienes and Tetraenes. Synth Common 1993, 23, 641. <http://dx.doi.org/10.1080/00397919308009822>
  • Ko Soo Y., Lee Albert W.M., Masamune Satoru, A. Reed Lawrence, Barry Sharpless K., Walker Frederick J.: Total synthesis of the L-hexoses. Tetrahedron 1990, 46, 245. <http://dx.doi.org/10.1016/S0040-4020(01)97596-9>
  • Ideses Rut, Shani Arnon: The Wittig reaction: comments on the mechanism and application as a tool in the synthesis of conjugated dienes. Tetrahedron 1989, 45, 3523. <http://dx.doi.org/10.1016/S0040-4020(01)81031-0>
  • Wenfang Huang, Jun Zhu, Wenjing Xiao, Yanneng Denc: Studies on the Wittig Reaction (VIII). Stereoselectivity of Diphenyl Allylic Phosphonium Ylids in Wittig Reaction. Phosphorus Sulfur Silicon Relat Elem 1989, 46, 99. <http://dx.doi.org/10.1080/10426508909412054>
  • Kumar Vijay, Dev Sukh: Chemistry of Ayurvedic Crude Drugs — VII guggulu (Resin From Commiphora Mukul) —6. Tetrahedron 1987, 43, 5933. <http://dx.doi.org/10.1016/S0040-4020(01)87799-1>
  • Daniel H., Le Corre M.: Stereoselectivite de la reaction de Wittig. Utilisation d'une phosphine portant un groupement nucleophile. Tetrahetron Lett 1987, 28, 1165. <http://dx.doi.org/10.1016/S0040-4039(00)95316-4>
  • Breuer Eli, Moshe Ruth: Stereoselectivity in the Wittig-Horner-Emmons Synthesis of Vinylphosphonates by the Reaction of Acylphosphonates with Acyclic or Heterocyclic Phosphonoacetates. Isr. J. Chem. 1986, 27, 45. <http://dx.doi.org/10.1002/ijch.198600008>
  • 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>
  • Jurczak Janusz, Pikul Stanislaw, Bauer Tomasz: Tetrahedron report number 195 (R)- and (S)-2,3-0-isopropylideneglyceraldehyde in stereoselective organic synthesis. Tetrahedron 1986, 42, 447. <http://dx.doi.org/10.1016/S0040-4020(01)87445-7>
  • 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, 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>
  • Zumbrunn Albrecht, Uebelhart Peter, Eugster Conrad Hans: Synthesen von Carotinen mit ψ-Endgruppen und (Z)-Konfiguration an terminalen konjugierten Doppelbindungen. HCA 1985, 68, 1519. <http://dx.doi.org/10.1002/hlca.19850680604>
  • Saalfrank Rolf W.: “Push-Pull” Substituted Allenes. Isr. J. Chem. 1985, 26, 181. <http://dx.doi.org/10.1002/ijch.198500091>
  • 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>
  • McEwen W. E., Beaver B. D., Cooney J. V.: MECHANISMS OF WITTIG REACTIONS; A NEW POSSIBILITY FOR SALT-FREE REACTIONS. Phosphorous and Sulfur and the Related Elements 1985, 25, 255. <http://dx.doi.org/10.1080/03086648508072742>
  • McEwen W. E., Beaver B. D.: ROLE OF THROUGH-SPACE 2p–3d OVERLAP EFFECTS IN LITHIUM-ION CATALYZED WITTIG REACTIONS. Phosphorous and Sulfur and the Related Elements 1985, 24, 259. <http://dx.doi.org/10.1080/03086648508074237>
  • Leininger Hartmut, Christl Manfred, Wendisch Detlef: Über die Oxidation von Benzvalen mit Singulett-Sauerstoff zum Bicyclo[1.1.0]butan-endo,endo-2,4-dicarbaldehyd. Chem Ber 1983, 116, 681. <http://dx.doi.org/10.1002/cber.19831160226>
  • 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>
  • Barrière Jean-Claude, Cléophax Jeanine, Géro Stephan D., Vuilhorgne Marc: Synthèse de composés cyclopentaniques chiraux, di, tri et tétrasubstitués. Application à la synthèse de dérivés Oxa-13-prostanoïques. HCA 1983, 66, 1392. <http://dx.doi.org/10.1002/hlca.19830660508>
  • Salzer Albrecht, Hafner Andreas: New Synthetic Routes to β-Olefinic Triphenylphosphonium Saltsvia (Diolefin)tricarbonyliron Complexes. HCA 1983, 66, 1774. <http://dx.doi.org/10.1002/hlca.19830660616>
  • 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>
  • Larsen Rolf Olaf, Aksnes Gunnar: KINETIC STUDY OF THE HORNER-REACTION. I. Phosphorous and Sulfur and the Related Elements 1983, 15, 219. <http://dx.doi.org/10.1080/03086648308073297>
  • Larsen Rolf Olaf, Aksnes Gunnar: THE EFFECT OF THE PHOSPHORYL SUBSTITUENTS ON THE STEREOCHEMISTRY OF THE HORNER REACTION. Phosphorous and Sulfur and the Related Elements 1983, 16, 339. <http://dx.doi.org/10.1080/03086648308080488>
  • 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, 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>
  • 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>
  • 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>
  • 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>
  • Hercouet A., le Corre M.: Acyloxyalkylidènephosphoranes—I. Tetrahedron 1981, 37, 2855. <http://dx.doi.org/10.1016/S0040-4020(01)92355-5>
  • hercouet A., Le corre M.: Acyloxyalkylidènephosphoranes—II. Tetrahedron 1981, 37, 2861. <http://dx.doi.org/10.1016/S0040-4020(01)92356-7>
  • Hercouet A., Le Corre M.: Acyloxyalkylidènephosphoranes—III. Tetrahedron 1981, 37, 2867. <http://dx.doi.org/10.1016/S0040-4020(01)92357-9>
  • 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>
  • Saalfrank Rolf W., Paul Winfried, Liebenow Heide: Die Ambiphilie von 1,1-Diethoxy-4,4,4-trifluor-3-(trifluormethyl)-1,2-butadien. Angew Chem 1980, 92, 740. <http://dx.doi.org/10.1002/ange.19800920914>
  • Canevet Claude, Röder Thomas, Vostrowsky Otto, Bestmann Hans Jürgen: Pheromone, XXVIII. Stereoselektive Synthese (E)-olefinischer Schmetterlingspheromone. Chem Ber 1980, 113, 1115. <http://dx.doi.org/10.1002/cber.19801130330>
  • Saalfrank Rolf W., Ackermann Erich, Winkler Herbert, Paul Winfried, Böhme Reinhild: „Push-pull”-substituierte Allene, IV. Synthese und Eigenschafteno-chinoider Donor/Akzeptorsubstituierter Allene Kristall- und Molekülstruktur vonE-2,2,2′,2′-Tetraethoxy-Δ3,3′(2H,2′H)-bi[phenanthro[9,10-b]furan]. Chem Ber 1980, 113, 2950. <http://dx.doi.org/10.1002/cber.19801130912>
  • Saalfrank Rolf W., Paul Winfried, Schierling Peter: „Push-pull”-substituierte Allene, VI. Darstellung und Eigenschaften von 1,1-Diethoxy-3-acylallenen. Chem Ber 1980, 113, 3477. <http://dx.doi.org/10.1002/cber.19801131106>
  • Bestmann Hans Jürgen, Frey Herbert: Reationen mit Phosphinalkylenen, XXXIX. Neue Aufbaumöglichkeiten für 1-Bromacetylene und aromatische sowie konjugierte Enine. Liebigs Ann Chem 1980, 1980, 2061. <http://dx.doi.org/10.1002/jlac.198019801216>
  • Bestmann Hans Jürgen, Roth Kurt, Ettlinger Manfred: Stereoselektive Synthese fürZ-α, β-ungesättigte Aldehyde. Angew Chem 1979, 91, 748. <http://dx.doi.org/10.1002/ange.19790910921>
  • Bestmann Hans Jürgen, Roth Kurt, Wilhelm Eberhard, Böhme Reinhild, Burzlaff Hans: Struktur des Primäraddukts aus einem Phosphorylid und Fluorenon. Angew Chem 1979, 91, 945. <http://dx.doi.org/10.1002/ange.19790911129>
  • Bestmann Hans Jürgen, Roth Kurt, Ettlinger Manfred: Stereoselective Synthesis ofZ-α,β-Unsaturated Aldehydes. Angew Chem Int Ed Engl 1979, 18, 687. <http://dx.doi.org/10.1002/anie.197906871>
  • Bestmann Hans Jürgen, Roth Kurt, Wilhelm Eberhard, Böhme Reinhild, Burzlaff Hans: Structure of the Primary Adduct of a Phosphorus Ylide and Fluorenone. Angew Chem Int Ed Engl 1979, 18, 876. <http://dx.doi.org/10.1002/anie.197908761>
  • Bestmann Hans Jürgen, Rösel Peter, Vostrowsky Otto: Pheromone, XXV. Alkylverzweigte Analoge von Lepidopterenpheromonen. Liebigs Ann Chem 1979, 1979, 1189. <http://dx.doi.org/10.1002/jlac.197919790813>