β-Halovinyl ketones: Synthesis from acetylenic ketones

✍ Scribed by Mikio Taniguchi; Shozo Kobayashi; Masako Nakagawa; Tohru Hino; Yoshito Kishi

• Publisher: Elsevier Science
• Year: 1986
• Tongue: French
• Weight: 189 KB
• Volume: 27
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)85059-5

✦ Synopsis

The reaction of terminal acetylenic ketones with NaI or LiBr gave almost exclusively E-B-iodo-or E-8-bromovinyl ketones in trifluoroacetic acid, while Z-Biodo-or Z-B-bromovinyl ketones were the major products in acetic acid. Trimethylsilyl iodide and oromide reacted smoothly with acetylenic ketones at -78°C to give TMS-allenolates which were readily converted to B-iodo-and B-bromovinyl ketones, respectively. B-Halovinyl ketones have proved to be versatile and valuable materials in organic synthe-