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Efficient thioacetalisation of carbonyl compounds

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Abstract

The thioacetalisation of a variety of heterocyclic, aromatic, and aliphatic carbonyl compounds (1 mmol) with ethane-1,2-dithiol (1 mmol) using silica sulphuric acid (SSA) is presented as an efficient heterogeneous catalyst under mild and solvent-free conditions at 60°C. The thioacetals were formed within a short reaction time (1–34 min) and isolated with 90–98 % yield following an extractive procedure and chromatography on silica gel. The competitive protection reaction between aldehyde and ketone with ethane-1,2-dithiol afforded the protected derivatives of benzaldehyde and acetophenone with 92 % and 8 % yields, respectively, indicating some selectivity.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Davood Habibi & Payam Rahmani

  2. Central Laboratory, Jam Petrochemical Company, Assaluyeh, Bushehr, P.O. Box 75391-415, Iran

    Ziba Akbaripanah

Authors
  1. Davood Habibi
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  2. Payam Rahmani
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  3. Ziba Akbaripanah
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Correspondence to Davood Habibi.

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Habibi, D., Rahmani, P. & Akbaripanah, Z. Efficient thioacetalisation of carbonyl compounds. Chem. Pap. 68, 417–421 (2014). https://doi.org/10.2478/s11696-013-0443-4

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  • DOI: https://doi.org/10.2478/s11696-013-0443-4

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