Tetrahedron Letters p. 4763 - 4766 (1986)
Update date:2022-08-05
Topics:
Taniguchi, Mikio
Kobayashi, Shozo
Nakagawa, Masako
Hino, Tohru
Kishi, Yoshito
The reaction of terminal acetylenic ketones with NaI or LiBr gave almost exclusively E-β-iodo-or E-β-bromovinyl ketones in trifluoracetic acid, while Z-β-iodo or Z-β-bromovinyl ketones were the major products in acetic acid.Trimethylsilyl iodide and bromide reacted smoothly with acetylenic ketones at -78 deg C to give TMS-allenolates which were readily converted to β-iodo and β-bromovinyl ketones, respectively.
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