Stereoselective Synthesis
and X-ray Structures of Alkenyliodonium Salts with a Pyridine N-Oxide Moiety

Michael W. Justik; Samantha L. Kristufek; John D. Protasiewicz; Nihal Deligonul

doi:10.1055/s-0029-1218791

SHORTPAPER

Stereoselective Synthesis and X-ray Structures of Alkenyliodonium Salts with a Pyridine N-Oxide Moiety

Michael W. Justik*^a, Samantha L. Kristufek^a, John D. Protasiewicz^b, Nihal Deligonul^b
^a School of Science, Penn State Erie, 4205 College Drive, Erie, PA 16563-0203, USA
Fax: +1(814)8986213; e-Mail: mwj10@psu.edu;
^b Department of Chemistry, Case Western Reserve University, 10900 Euclid Avenue, Cleveland, OH 44106, USA

Abstract

All articles of this category

Abstract

A concise preparation and characterization of substituted 1-{[(Z)-1-phenyl-2-phenyliodonio)vinyl]oxy}pyridinium ditosylates is presented. Determination of the X-ray crystal structure reveals a pseudo-square planar molecular geometry about iodine.

Key words

hypervalent iodine - alkynyliodonium salts - iodonium ylides - alkenyliodonium salts - X-ray crystallography

Full Text

References

<A NAME="RM01410SS-1A">1a</A> Zhdankin VV. Stang PJ. Chem. Rev. 2008, 108: 5299

<A NAME="RM01410SS-1B">1b</A> Koser GF. In Advances in Heterocyclic Chemistry Vol. 84: Katritzky A. Elsevier; Oxford: 2004. p.225

<A NAME="RM01410SS-1C">1c</A> Feldman KS. ARKIVOC 2003, (vi): 179

<A NAME="RM01410SS-1D">1d</A> Zhdankin VV. Stang PJ. Chem. Rev. 2002, 102: 2523

<A NAME="RM01410SS-1E">1e</A> Zhdankin VV. Stang PJ. Tetrahedron 1998, 54: 10927

<A NAME="RM01410SS-1F">1f</A> Stang PJ. Zhdankin VV. Chem. Rev. 1996, 96: 1123

<A NAME="RM01410SS-1G">1g</A> Koser GF. In The Chemistry of Functional Groups, Suppl. D2 Patai S. Rappoport Z. Wiley-Interscience; Chichester: 1995. p.1173

<A NAME="RM01410SS-2">2</A> Ochiai M. Kunishima M. Nagao Y. Fuji K. Shiro M. Fujita E. J. Am. Chem. Soc. 1986, 108: 8281

<A NAME="RM01410SS-3">3</A> Kitamura T. Mansei Y. Fujiwara Y. J. Organomet. Chem. 2002, 646: 196

<A NAME="RM01410SS-4">4</A> Stang PJ. Murch P. Tetrahedron Lett. 1997, 38: 8793

<A NAME="RM01410SS-5">5</A> Kitamura T. Zheng L. Fukuoka T. Fujiwara Y. Taniguchi H. Sakurai M. Tanaka R. J. Chem. Soc., Perkin Trans. 1 1997, 1511

<A NAME="RM01410SS-6">6</A> Kitamura T. Tsuda K. Fujiwara Y. Tetrahedron Lett. 1998, 39: 5375

<A NAME="RM01410SS-7">7</A> Shu T. Chen D.-W. Ochiai M. Tetrahedron Lett. 1996, 37: 5539

Using 7b as a nucleophile, the observed decomposition products included iodobenzene, protonated 4-picoline N-oxide, and an intractable mixture of minor products.

<A NAME="RM01410SS-9">9</A> Kleinpeter E. J. Serb. Chem. Soc. 2006, 71: 1

Crystallographic data for 9b has been deposited with the Cambridge Crystallographic Data Centre (CCDC 760557). Copies of this information can be obtained free of charge via www.ccdc.cam.ac.uk.

<A NAME="RM01410SS-11A">11a</A> Ochiai M. Kunishima M. Fuji K. Shiro M. Nagao Y. J. Chem. Soc., Chem. Commun. 1988, 1076

<A NAME="RM01410SS-11B">11b</A> Ochiai M. Sumi K. Takaoka Y. Kunishima M. Fuji K. Nagao Y. Shiro M. Fujita E. Tetrahedron 1988, 44: 4095

<A NAME="RM01410SS-11C">11c</A> Chekhlov AN. Gafurov RG. Pomytkin IA. Martynov IV. Aleinikov NN. Kashtanov SA. Dubovitskii FI. Dokl. Akad. Nauk SSSR 1986, 291: 1040

<A NAME="RM01410SS-12A">12a</A> Stang PJ. Wingert H. Arif AM. J. Am. Chem. Soc. 1987, 109: 7235

<A NAME="RM01410SS-12B">12b</A> Zefirov NS. Koz’min AS. Kasumov T. Potekhin KA. Sorokin VD. Brel VK. Abramkin EV. Struchkov YuT. Zhdankin VV. Stang PJ. J. Org. Chem. 1992, 57: 2433

<A NAME="RM01410SS-13">13</A> Landrum GA. Hoffmann R. Angew. Chem. Int. Ed. 1998, 37: 1887

<A NAME="RM01410SS-14">14</A> Margida AJ. Koser GF. J. Org. Chem. 1984, 49: 4703