Issue 11, 2007
From the journal:

Chemical Communications

Oxygenation vs iodonio substitution during the reactions of alkenylsilanes with iodosylbenzene: participation of the internal oxy group†

Morifumi Fujita,*a   Hee Jin Lee,a   Takashi Sugimuraa  and  Tadashi Okuyamaa  

* Corresponding authors

a Graduate School of Material Science, Himeji Institute of Technology, University of Hyogo, 3-2-1 Kohto, Kamigori, Japan
E-mail: fuji@sci.u-hyogo.ac.jp
Fax: +81-791-58-0115
Tel: +81-791-58-0170

Abstract

Reaction of 4-acyloxybut-1-enylsilanes with iodosylbenzene in the presence of BF3·OEt2 gave 4-acyloxy-2-oxobutylsilane and 3-acyloxytetrahydrofuran-2-ylsilane via a 1,3-dioxan-2-yl cation intermediate, which is generated by participation of the acyloxy group during the electrophilic addition of iodine(III) to the substrate.

Graphical abstract: Oxygenation vs iodonio substitution during the reactions of alkenylsilanes with iodosylbenzene: participation of the internal oxy group

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Article information

DOI
https://doi.org/10.1039/B615888A
Article type
Communication
Submitted
01 Nov 2006
Accepted
08 Dec 2006
First published
10 Jan 2007

Chem. Commun., 2007, 1139-1141

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Oxygenation vs iodonio substitution during the reactions of alkenylsilanes with iodosylbenzene: participation of the internal oxy group

M. Fujita, H. J. Lee, T. Sugimura and T. Okuyama, Chem. Commun., 2007, 1139 DOI: 10.1039/B615888A

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