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Synlett 2000; 2000(12): 1798-1800
DOI: 10.1055/s-2000-8684
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N-Bromosuccinimide (NBS), an Efficient Reagent for the Conversion of 1,3-Oxathiolanes to Carbonyl Compounds

Babak Karimi* , Hassan Seradj, Mohammad H. Tabaei
  • *Department of Chemistry, Institute for Advanced Studies in Basic Sciences (IASBS), P. O. Box 45195-159, Gava Zang, Zanjan, Iran; Fax +98(0241)44 90 23; E-mail: karimi@iasbs.ac.ir
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Publication Date:
31 December 2000 (online)

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Various types of 1,3-oxathiolanes of aromatic and aliphatic carbonyl compounds, including those obtained from α,β-unsaturated aldehydes were efficiently converted to the corresponding carbonyl compounds in the presence of NBS (0.4-0.9 equiv.) under mild reaction conditions. The method was also effectively applied to the chemoselective deprotection of 1,3-oxathiolanes in the presence of 1,3-dioxolanes.

1,3-oxathiolanes - O,S-acetals - deprotection - N-bromosuccinimide - cleavage