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Paper | Regular issue | Vol 75, No. 3, 2008, pp.599-609
Published online, 22nd November, 2007
DOI: 10.3987/COM-07-11244
A Facile Synthesis of 1,3-Dihydroisobenzofurans Using Iodocylization of 2-Vinylbenzyl Alcohols

Kazuhiro Kobayashi,* Kazuaki Shikata, Shuhei Fukamachi, and Hisatoshi Konishi

*Department of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan


An efficient route for the preparation of 1,3-dihydroisobenzofurans based on the iodine-mediated cyclization of 2-vinylbenzyl alcohols, which can be prepared feasibly by reactions of 2-vinylphenyllithiums with carbonyl compounds, is reported. Substitution reactions of the iodo moiety of the resulting 1-(iodomethyl)-1,3-dihydroisobenzofurans with tributyltin hydride and sodium thiolates are also described.