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Communication | Regular issue | Vol 57, No. 11, 2002, pp.1989-1995
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9616
A New Simple Method for the Synthesis of Thiophene Derivatives — Generation of Thiocarbonyl Ylides form S-α-(Dimethylphenylsilyl)benzyl Acylates and Their Cycloaddition with Acetylenic Dipolarophiles —

Mitsuo Komatsu,* Jinil Choi, Masatoshi Mihara, Yoji Oderaotoshi, and Satoshi Minakata

*Department of Applied Chemistry, Graduate School of Science, Osaka University, 2-1 Yamadaoka, Suita, Osaka 560-0871, Japan


The cycloaddition of S-α-(dimethylphenylsilyl)benzyl acylates (1) with acetylenic dipolarophiles via 1,4-silatropy proceeded readily to afford thiophene derivatives. The reaction of thioesters (1) with 1-diethylamino-1- propyne (A), an electron-rich acetylenic dipolarophile, gave 5-aryl-3- diethylamino-4-methyl-2-phenylthiophenes (3) and 4-aryl-2-diethylamino- 3-methyl-5-phenylthiophenes (4). When dimethyl acetylenedicarboxylate (DMAD), an electron-deficient alkyne, was used, the reaction of thioesters (1) afforded thiophene derivatives (4) exclusively.