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Note | Regular issue | Vol 81, No. 3, 2010, pp.699-705
Published online, 28th December, 2009
DOI: 10.3987/COM-09-11869
Synthesis of 1,2-Dihydro-3-benzoxepins by the Reaction of 2-Lithio-β-methoxystyrenes with Epoxides Followed by Hydriodic Acid Catalyzed Cyclization

Kazuhiro Kobayashi,* Hiroo Hashimoto, Toshiyuki Nagaoka, Yuu Shirai, and Hisatoshi Konishi

*Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan


5-Substituted 1,2-dihydro-3-benzoxepins can be prepared in reasonable overall yields from α-substituted 2-bromo-β-methoxystyrenes. Thus, the reaction of α-substituted 2-lithio-β-methoxystyrenes, generated by the bromine-lithium exchange between α-substituted 2-bromo-β-methoxystyrenes and butyllithium, with epoxides gives the corresponding 2-(methoxyvinyl)phenethyl alcohols. These undergo cyclization with a loss of methanol on treatment with a catalytic amount of hydriodic acid to give the desired products.