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Synthetic Communications

An International Journal for Rapid Communication of Synthetic Organic Chemistry

Volume 13, 1983 - Issue 14

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Unexpected Solvent Effect of HMPA. Directed Selectivity of a Semistabilized Arsonium Ylide towards Carbonyl Compounds: The Case of Cinnamyl Triphenylarsonate

J. B. Ousset Laboratoire de Stéréochimie de l'Ecole Nationale Supérieure de Chimie (ERA 687), Université Louis Pasteur, 67008, Strasbourg, France

C. Mioskowski Laboratoire de Stéréochimie de l'Ecole Nationale Supérieure de Chimie (ERA 687), Université Louis Pasteur, 67008, Strasbourg, France

G. Solladié Laboratoire de Stéréochimie de l'Ecole Nationale Supérieure de Chimie (ERA 687), Université Louis Pasteur, 67008, Strasbourg, France

Pages 1193-1196 | Published online: 05 Dec 2006

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https://doi.org/10.1080/00397918308063732

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Madhavan Jaccob & Ponnambalam Venuvanalingam. (2013) Mechanism and diastereoselectivity of arsenic ylide mediated cyclopropanation: a theoretical study. RSC Advances 3:39, pages 17793.
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Christian Reichardt & Thomas Welton. 2010. Solvents and Solvent Effects in Organic Chemistry. Solvents and Solvent Effects in Organic Chemistry 587 673 .

Louis F. Fieser, Mary Fieser & Tse‐Lok HoTse‐Lok Ho, Mary Fieser, Rick Danheiser, William Roush, Janice Smith & Louis Fieser. 2006. Fieser and Fieser's Reagents for Organic Synthesis. Fieser and Fieser's Reagents for Organic Synthesis.

Hong Jiang, Xianming Deng, Xiuli Sun, Yong Tang & Li-Xin Dai. (2005) Highly Stereoselective Synthesis of Trisubstituted Vinylcyclopropane Derivatives via Arsonium Ylides. The Journal of Organic Chemistry 70:24, pages 10202-10205.
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P. Savignac, B. Iorga & M. Savignac. 2005. Comprehensive Organic Functional Group Transformations II. Comprehensive Organic Functional Group Transformations II 723 759 .

Ren-Hua Fan, Xue-Long Hou & Li-Xin Dai. (2004) Formation of P-Ylide under Neutral and Metal-Free Conditions: Transformation of Aziridines and Epoxides to Conjugated Dienes In the Presence of Phosphine. The Journal of Organic Chemistry 69:3, pages 689-694.
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Robert R. Dykstra. 2001. Encyclopedia of Reagents for Organic Synthesis. Encyclopedia of Reagents for Organic Synthesis.

Yao-Zeng Huang, Yong Tang & Zhang-Lin Zhou. (1998) Synthetic applications of organotelluronium salts. Tetrahedron 54:9, pages 1667-1690.
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André Seyer, Lilian Alcaraz & C. Mioskowski. (1997) Olefination of activated halides and mesylates using arsonium ylides. Tetrahedron Letters 38:45, pages 7871-7874.
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Yong Tang, Yao-Zeng Huang, Li-Xin Dai, Jie Sun & Wei Xia. (1997) An Efficient Stereocontrolled Strategy in the Cyclopropanation Reactions of α,β-Unsaturated Ketones with Semistabilized Ylides: Highly Selective Synthesis of Two Geometrical Isomers of Vinyl-Substituted Cyclopropane Derivatives. The Journal of Organic Chemistry 62:4, pages 954-959.
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Frédéric Werner, Gilles Parmentier, Bang Luu & Laurence Dinan. (1996) A convenient stereoselective synthesis of castasterone and its analogues using arsenic ylides. Tetrahedron 52:15, pages 5525-5532.
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. 1996. Comprehensive Heterocyclic Chemistry II. Comprehensive Heterocyclic Chemistry II 1215 1369 .

Ihsan Erden. 1996. Comprehensive Heterocyclic Chemistry II. Comprehensive Heterocyclic Chemistry II 97 144 .

. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 1147 1316 .

Ian Gosney & Douglas Lloyd. 1995. Comprehensive Organic Functional Group Transformations. Comprehensive Organic Functional Group Transformations 719 770 .

J.J. Harnett, L. Alcaraz, C. Mioskowski, J.P. Martel, T. Le Gall, Dong-Soo Shin & J.R. Falck. (1994) A novel synthesis of homologated allylic alcohols using dimethylsulphonium methylide. Tetrahedron Letters 35:13, pages 2009-2012.
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Boris A Cheskis, Natalya M Ivanova, Aiexsander M Moiseenkov & Oleg M Nefedov. (1993) The chemistry of acetylcyclopropane. Russian Chemical Reviews 62:4, pages 337-358.
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Jeffrey Aubé. 1991. Comprehensive Organic Synthesis. Comprehensive Organic Synthesis 819 842 .

Philippe Chabert & Charles Mioskowski. (1989) (5,5-diethoxy-2-(E)-pentenyl) triphenylarsonium ylide: A new synthetic equivalent of δ-formyl butadienylanion. Tetrahedron Letters 30:44, pages 6031-6034.
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B. Boubia, C. Mioskowski, S. Manna & J.R. Falck. (1989) Homologation of aldehydes using (phenylthiomethylene) triphenylarsorane: selective preparation of α-thiophenoxyepoxides and phenylthioenol ethers. Tetrahedron Letters 30:44, pages 6023-6026.
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P. Chabert, J.B. Ousset & C. Mioskowski. (1989) (3,3-Diisopropoxypropyl)triphenylarsonium ylide: A new synthetic equivalent of β-formyl vinyl anion. Tetrahedron Letters 30:2, pages 179-182.
Crossref

J. B. OUSSET, C. MIOSKOWSKI & G. SOLLADIE. (2016) ChemInform Abstract: UNEXPECTED SOLVENT EFFECT OF HMPA. DIRECTED SELECTIVITY OF A SEMISTABILIZED ARSONIUM YLIDE TOWARDS CARBONYL COMPOUNDS: THE CASE OF CINNAMYLTRIPHENYLARSONATE. Chemischer Informationsdienst 15:36.
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Unexpected Solvent Effect of HMPA. Directed Selectivity of a Semistabilized Arsonium Ylide towards Carbonyl Compounds: The Case of Cinnamyl Triphenylarsonate

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Unexpected Solvent Effect of HMPA. Directed Selectivity of a Semistabilized Arsonium Ylide towards Carbonyl Compounds: The Case of Cinnamyl Triphenylarsonate

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