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Synthesis 2010(14): 2345-2347  
DOI: 10.1055/s-0029-1218791
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Michael W. Justik*a, Samantha L. Kristufeka, John D. Protasiewiczb, Nihal Deligonulb
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
Further Information

Publication History

Received 19 February 2010
Publication Date:
20 May 2010 (online)

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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

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8

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

10

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.