Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.