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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 5, 1975 - Issue 1
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Original Articles

Cyclopentenones from β, ε-Diketo Phosphonates. Synthesis of cis-Jasmone

Robin D. Clark Department of Chemistry, University of California, Berkeley, California, 94720
,
Leland G. Kozar Department of Chemistry, University of California, Berkeley, California, 94720
&
Clayton H. Heathcock Department of Chemistry, University of California, Berkeley, California, 94720
Pages 1-5 | Received 05 Sep 1974, Published online: 05 Dec 2006

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Didier Villemin, Fabrice Simeon, Hugues Decreus & Paul-Alain Jaffres. (1998) RAPID AND EFFICIENT ARBUZOV REACTION UNDER MICROWAVE IRRADIATION. Phosphorus, Sulfur, and Silicon and the Related Elements 133:1, pages 209-213.
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A. M. M. M. Phillips, M.J. Mphahlele, A.M. Modro, T.A. Modro & A. Zwierzak. (1992) PHOSPHONIC SYSTEMS. 7. REACTIONS OF 2,3-EPOXYPHOSPHONATES WITH NUCLEOPHILES: PREPARATION OF 2,3-DISUBSTITUTED ALKYLPHOSPHONIC ESTERS AND RELATED SYSTEMS. Phosphorus, Sulfur, and Silicon and the Related Elements 71:1-4, pages 165-174.
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J.P. Haelters & B. Corbel et G. Sturtz. (1989) CHLORO-1 ET CHLORO-3 METHOXYCARBONYLHYDRAZONO-2 PROPYLPHOSPHONATES: REACTIFS D'ALKYLATION D'ENOLATES DE CETONES. ACCES A DES PHOSPHONATES PYRROLIQUES ET A DES β,ε DICETOPHOSPHONATES PRECURSEURS DE CYCLOPENTENONES. Phosphorus, Sulfur, and Silicon and the Related Elements 44:1-2, pages 53-74.
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F. Kuo & P.L. Fuchs. (1986) Use of 1-Penten-3-One-4- Phosphonate as a Kinetic Ethyl Vinyl Ketone Equivalent in the Robinson Annulation Reaction1 . Synthetic Communications 16:14, pages 1745-1759.
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Elie Elia Aboujaoude, Noël Collignon, Marie-Paule Teulade & Philippe Savignac. (1985) PREPARATION QUASI QUANTITATIVE DE PHOSPHONATES β-CARBONYLES PAR L ' EMPLOI D ' UNE BASE RELAIS, LE DIPAL [(i-C3H7)2NLi]. Phosphorus and Sulfur and the Related Elements 25:1, pages 57-61.
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Tse-Lok Ho. (1977) Dihydrojasmone Synthesis. Pyrolytic Cleavage of a Cyclopropyl Ketone. Synthetic Communications 7:5, pages 351-354.
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Articles from other publishers (38)

Zhigang Liu, Miaolin Ke, Ke Zhang, Zexu Wang, Baijun Ye & Fener Chen. (2021) Palladium‐Catalyzed Allylation of Vinylethylene Carbonates with β ‐Ketophosphonates: Stereoselective Synthesis of ( Z )‐Homoallylic Phosphonates . ChemCatChem 13:7, pages 1753-1762.
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Zhigang Liu, Miaolin Ke, Ke Zhang, Sheng Zuo, Meifen Jiang & Fener Chen. (2021) Stereoselective Synthesis of ( Z )‐Dihomoallylic Phosphonates with Quaternary Carbon Center by Palladium‐Catalyzed Bisallylation of Vinylethyene Carbonates with β ‐Ketophosphonates . Asian Journal of Organic Chemistry 10:4, pages 757-761.
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Jing Feng, Tianzi Yu, Zhijiang Zhang, Jinpeng Li, Shaomin Fu, Juan Chen & Bo Liu. (2018) Asymmetric synthesis of the fully functionalized six-membered ring of trigoxyphin A. Chemical Communications 54:55, pages 7665-7668.
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D. Ravikumar, Ch. Subramanyam, S. Mohan, D. Chandra Sekhar & K. Prasada Rao. (2018) Nano BF3.SiO2 catalysed, microwave assisted Michaelis-Arbuzov reaction to synthesize biologically active phosphonates under solvent-free condition. Materials Today: Proceedings 5:12, pages 25832-25842.
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Gangaram Pallikonda, Swamy Maloth, Sathish Kumar Kurapati, M. Zubair Khalid Baig, Akhil Raj Kumar Saraswathi, Subhas Ghosal & Manab Chakravarty. (2015) New ω-ketovinyl phosphonates: inexpensive synthesis, isomerization studies and route for functionalized 1,3-butadienes. Tetrahedron 71:34, pages 5538-5546.
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Petr Jansa, Antonín Holý, Martin Dračinský, Ondřej Baszczyňski, Michal Česnek & Zlatko Janeba. (2011) Efficient and ‘green’ microwave-assisted synthesis of haloalkylphosphonates via the Michaelis–Arbuzov reaction. Green Chemistry 13:4, pages 882.
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György Keglevich, Alajos Grün, Zsófia Blastik & István Greiner. (2011) Solid–liquid phase alkylation of P=O–functionalized CH acidic compounds utilizing phase transfer catalysis and microwave irradiation. Heteroatom Chemistry 22:2, pages 174-179.
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Bingli Yan & Christopher D. Spilling. (2008) Synthesis of Cyclopentenones via Intramolecular HWE and the Palladium-Catalyzed Reactions of Allylic Hydroxy Phosphonate Derivatives. The Journal of Organic Chemistry 73:14, pages 5385-5396.
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Nikolay T. Tzvetkov, Torsten Arndt & Jochen Mattay. (2007) Synthesis of angularly fused cyclopentanoids and analogous tricycles via photoinduced ketyl radical/radical anion fragmentation–cyclization reactions. Tetrahedron 63:42, pages 10497-10510.
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Louis F. Fieser, Mary Fieser & Tse‐Lok HoTse‐Lok Ho, Mary Fieser & Louis Fieser. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.
Nikolay T. Tzvetkov, Beate Neumann, Hans‐Georg Stammler & Jochen Mattay. (2006) Photoreactions of Tricyclic α‐Cyclopropyl Ketones and Unsaturated Enones – Synthesis of Polyquinanes and Analogous Ring Systems. European Journal of Organic Chemistry 2006:2, pages 351-370.
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Nikolay Tzvetkov, Marc Schmidtmann, Achim Müller & Jochen Mattay. (2003) Reductive PET-fragmentation–cyclization processes of bicyclo[n.3.0]alkanones: synthesis of angular quasi-triquinane and propellane systems. Tetrahedron Letters 44:32, pages 5979-5982.
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Philippe Savignac & Bogdan Iorga. 2003. Modern Phosphonate Chemistry. Modern Phosphonate Chemistry.
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Andrew Abell. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.
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Franck Raeppel, Jean-Marc Weibel & Denis Heissler. (1999) Synthesis of the trans-syn-trans perhydrobenz[e]indene moiety of the stellettins and of the stelliferins. Tetrahedron Letters 40:35, pages 6377-6381.
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Michael J. Taschner. 1989. Selectivities in Lewis Acid Promoted Reactions. Selectivities in Lewis Acid Promoted Reactions 227 246 .
Otohiko Tsuge, Shuji Kanemasa & Hiroyuki Suga. (1988) Synthesis of 2-(1-Phosphorylalkyl)- and 2-(1-Alkenyl)furans through Nitrile Oxide Cycloaddition Route. Bulletin of the Chemical Society of Japan 61:6, pages 2133-2146.
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Y. Koteswar Rao & M. Nagarajan. (1988) Synthesis of (±) silphinene. Tetrahedron Letters 29:1, pages 107-108.
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Naoyuki Satoh, Tatsuo Ishiyama, Norio Miyaura & Akira Suzuki. (1987) Stereoselective Synthesis of Conjugated Dienones via the Palladium-Catalyzed Cross-Coupling Reaction of 1-Alkenylboronates with 3-Halo-2-alken-1-ones. Bulletin of the Chemical Society of Japan 60:9, pages 3471-3473.
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Ronald L. Halterman & K.Peter C. Vollhardt. (1986) Practical synthesis of two annelated optically active cyclopentadienes from the chiral pool and their transition metal complexes. Tetrahedron Letters 27:13, pages 1461-1464.
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J.R Rocca, J.H Tumlinson, B.M Glancey & C.S Lofgren. (1983) Synthesis and stereochemistry of tetrahydro-3, 5-dimethyl-6-(1)methylbutyl)-2H-pyran-2-one, a component of the queen recognition pheromone of .. Tetrahedron Letters 24:18, pages 1893-1896.
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Hans‐Josef Altenbach & Rainer Korff. (2003) β,ε‐Dioxophosphonates by Reductive Nucleophilic Acylation of 1,3‐Dioxo Compounds: Facile Synthesis of Jasmones. Angewandte Chemie International Edition in English 21:5, pages 371-371.
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Hans‐Josef Altenbach & Rainer Korff. (2006) β,ϵ‐Dioxophosphonate durch reduktive nucleophile Acylierung von 1,3‐Dioxoverbindungen: Einfache Synthese von Jasmonen. Angewandte Chemie 94:5, pages 388-388.
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Ferdinand Näf & René Decorzant. (2004) An Efficient Synthesis of Methyl (±)‐Jasmonate and ( Z )‐Jasmone . Helvetica Chimica Acta 61:7, pages 2524-2529.
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R. D. CLARK, L. G. KOZAR & C. H. HEATHCOCK. (2016) ChemInform Abstract: CYCLOPENTENONES FROM BETA,EPSILON‐DIKETO PHOSPHONATES. SYNTHESIS OF CIS‐JASMONE. Chemischer Informationsdienst 6:29.
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