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Synthesis 2011(2): 347-351  
DOI: 10.1055/s-0030-1258367
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Hydrogen Peroxide or Peracetic Acid Mediated Self-Titrating α-Halogenation of 1,3-Dicarbonyl Compounds

Ramulu Akula, Marc J. Galligan, Hasim Ibrahim*
Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland
Fax: +353(1)7161178; e-Mail: hasim.ibrahim@ucd.ie;
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Publication History

Received 18 August 2010
Publication Date:
15 December 2010 (online)

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Abstract

Efficient oxidative α-halogenation of 1,3-dicarbonyl compounds has been achieved by employing a system comprising of sub-stoichiometric amounts of TiX4 (X = Cl, Br) in conjunction with environmentally benign hydrogen peroxide (H2O2) or peracetic acid (MeCO3H) as the oxidants. The end point of the reaction is accompanied by a sharp colour change.

Key words

halogenation - peroxides - titanium - halides - electrophilic

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22

For full analytical data of all products from Tables  [²] and  [³] with the exception of the products in Table  [²] , entry 7 and Table  [³] , entry 3, see reference 13.