A Novel One-Pot Conversion of Allyl Alcohols into Primary Allyl Halides Mediated by Acetyl Halide

✍ Scribed by Nurhan Kishali; M. Fatih Polat; Ramazan Altundas; Yunus Kara

• Publisher: John Wiley and Sons
• Year: 2008
• Tongue: German
• Weight: 157 KB
• Volume: 91
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200890014

✦ Synopsis

Abstract

A new and simple method for the synthesis of the primary allyl chlorides and bromides 9–16 from the secondary or tertiary allyl alcohols 3–8 and acyl halide was developed (Scheme 2, Table 1). Non‐commercially available secondary and tertiary allyl alcohols were synthesized from the related ketones and aldehydes via the addition of vinylmagnesium chloride. Mechanistic studies indicate that the alcohols were first acetylated by the acetyl halide and then protonated prior to substitution by the halide, Cl^−^ or Br^−^, via an S~N~2′ reaction, to yield the primary halides (Scheme 5).