New applications of organofluorine reagents in organic synthesis. III. A convenient synthetic method for acetylenic ethers and thioethers

✍ Scribed by Kiyoshi Tanaka; Shuichi Shiraishi; Takeshi Nakai; Nobuo Ishikawa

• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 241 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)94954-8

✦ Synopsis

Acetylenic ethers and thioethers have been well secured as versatile intermediates in organic synthesis for which there exists only a limited number of synthetic methodology. 1) In our continuing investigation of application of organofluorine reagents in organic synthesis, 2) we now wish to report an exceedingly convenient method for the preparation of acetylenic ethers (3_) and thioethers (5) from the reactions of 2,2,2-trifluoroethyl ethers (2 and thioethers (2) with various alkyllithium reagents (eq. 1). The formation of the acetylenic products from both ethers 1 and thioethers Liis of interest in view of the differing reactivities ofL and 2 toward lithium dialkylamides 3) hr