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Note | Regular issue | Vol 45, No. 11, 1997, pp.2261-2272
Published online, 1st January, 1970
DOI: 10.3987/COM-97-7946
Cesium Fluoride-mediated Claisen Rearrangements of Phenyl Propargyl Ethers: Substituent Effects of an ortho-Alkoxy Group on the Benzene Ring or Modified Propargyl Residues

Tsutomu Ishikawa,* Akiko Mizutani, Chizue Miwa, Yumie Oku, Naoko Komano (nee Ohkubo), Atsuya Takami, and Toshiko Watanabe

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan


The expected 7-alkoxy-2-emthylbenzo[b]furans were effectively given in the CsF-mediated Claisen rearrangement of phenyl propargyl ethers with an o-alkoxy substituent on the benzene ring. On the other hand CsF did not affect the production of the corresponding benzo[b]furans when ethers, carrying a propargyl residue modified by either 1,1-dimethyl or 3-ethoxycarbonyl functions, were used as substrates in the rearrangement.