Synthesis and Reactions of a Hypervalent Iodine-Benzyne Precursor Possessing an Ester Group

Tsugio Kitamura; Kanako Wasai; Mitsuru Todaka; Yuzo Fujiwara

doi:10.1055/s-1999-2734

Synlett 1999; 1999(6): 731-732
DOI: 10.1055/s-1999-2734

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Synthesis and Reactions of a Hypervalent Iodine-Benzyne Precursor Possessing an Ester Group

Tsugio Kitamura^* , Kanako Wasai, Mitsuru Todaka, Yuzo Fujiwara

^*Department of Chemistry and Biochemistry, Graduate School of Engineering, Kyushu University, Hakozaki, Fukuoka 812-8581, Japan; Fax +81-92-6 51-56 06; E-mail: tkitatcf@mbox.nc.kyushu-u.ac.jp

Abstract

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The Diels-Alder reaction of methyl 2-pyrone-5-carboxylate and bis(trimethylsilyl)acetylene gave methyl 3,4-bis(trimethylsilyl)-benzoate which was transformed into [5-(methoxycarbonyl)-2-(trimethylsilyl)phenyl](phenyl)iodonium triflate by the reaction with a hypervalent iodine reagent PhI(OAc)₂/TfOH. The generation and trapping reactions of 4-(methoxycarbonyl)-1,2-didehydrobenzene were successfully conducted by the reaction of the iodonium triflate with Bu₄NF.

hypervalent iodine compound - benzyne - Diels-Alder reaction - methyl 2-pyrone-5-carboxylate - bis(trimethylsilyl)acetylene

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