Volume 29, Issue 11
Heterocyclic Compounds
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ChemInform Abstract: [3 + 2] Cycloaddition Reactions of Alkynyl(phenyl)iodonium Triflates with Ethyl Diazoacetate, N-t-Butyl-α-phenyl Nitrone and t-Butylnitrileoxide as 1,3-Dipoles.

P. J. STANG

P. J. STANG

Dep. Chem., Univ. Utah, Salt Lake City, UT 84112, USA

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P. MURCH

P. MURCH

Dep. Chem., Univ. Utah, Salt Lake City, UT 84112, USA

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First published: 23 June 2010

Abstract

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ChemInform Abstract

Iodonium triflates undergo 1,3-dipolar cycloadditions with ethyl diazoacetate (II), the nitrone (V) and tert-butylnitrile oxide generated in situ from oxime (VIII) and iodosobenzene. Each reaction yields only a single regioisomer. Displacement of the iodonium moiety in the heterocycles (III), (VI), and (IX) by nucleophiles allows the preparation of functionalized systems.

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