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A Novel One‐Pot Conversion of Allyl Alcohols into Primary Allyl Halides Mediated by Acetyl Halide
Author(s) -
Kishali Nurhan,
Polat M. Fatih,
Altundas Ramazan,
Kara Yunus
Publication year - 2008
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200890014
Subject(s) - chemistry , halide , primary (astronomy) , yield (engineering) , protonation , organic chemistry , medicinal chemistry , tertiary alcohols , allyl alcohol , primary alcohol , alcohol , catalysis , ion , physics , materials science , astronomy , metallurgy
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 ).