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Synthesis 2010(14): 2355-2360  
DOI: 10.1055/s-0029-1218795
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Novel Preparation of Polymer-Supported Iodobenzene and Its Synthetic Utility as a Recyclable Reagent with m-Chloroperbenzoic Acid

Yuhsuku Suzuki, Hideo Togo*
Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
Fax: +81(43)2902792; e-Mail: togo@faculty.chiba-u.jp;
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Publikationsverlauf

Received 4 March 2010
Publikationsdatum:
20. Mai 2010 (online)

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Abstract

Three novel polymer-supported iodobenzene compounds A0, A6, and A10 were prepared from the reaction of commercially available cross-linked poly(p-chloromethyl)styrene with m-iodobenzylalcohol, 6-(m-iodobenzyloxy)-1-hexanol, and 10-(m-iodobenzyloxy)-1-decanol. Their catalytic reactivity and reusability for the oxidative α-tosyloxylation of ketones and the cyclization of N-methoxy-2-arylethanesulfonamides in the presence of m-chloroperbenzoic acid (mCPBA) were confirmed to provide α-tosyloxy­ketones and N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxides, respectively, in good yields.

Key words

polymer-supported PhI - recycle mCPBA - α-tosyloxy­ketone - ketone - N-methoxy-3,4-dihydro-2,1-benzothiazine-2,2-dioxide - catalyst

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