Tetrahedron letters

β-Halovinyl ketones: Synthesis from acetylenic ketones

M Taniguchi, S Kobayashi, M Nakagawa, T Hino…

Index: Taniguchi, Mikio; Kobayashi, Shozo; Nakagawa, Masako; Hino, Tohru; Kishi, Yoshito Tetrahedron Letters, 1986 , vol. 27, # 39 p. 4763 - 4766

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Citation Number: 55

Abstract

Abstract The reaction of terminal acetylenic ketones with NaI or LiBr gave almost exclusively E-β-iodo-or E-β-bromovinyl ketones in trifluoroacetic 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 C to give TMS-allenolates which were readily converted to β-iodo-and β-bromovinyl ketones, respectively.

~88%

~97%

~16%

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