The addition of trimethylsilyl iodide to some α,β-unsaturated ketones

✍ Scribed by R.D. Miller; D.R. McKean

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 234 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)93958-9

✦ Synopsis

Haloketones and derivatives are extremely useful materials for Organic Synthesis. We describe here the facile preparation of S and y-iodoketones by the addition of trimethylsilyl iodide to a variety of a,S-unsaturated and cyclopropyl ketones. S-Haloketones are useful substrates in Organic Synthesis as precursors to enones, as substrates in annulation reactions, for the generation of heterocyclic derivatives and for reductive coupling to generate dicarbonyl derivatives.

1 Although some newer preparative techniques have appeared recently, 2 the chlorides and bromides have often been prepared by the acylation of olefins.la'3 Less frequently these compounds have been generated directly by the addition to HK to specific a,B-unsaturated ketones.