ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Efficient thioacetalisation of carbonyl compounds

Davood Habibi, Payam Rahmani, and Ziba Akbaripanah

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

E-mail: davood.habibi@gmail.com

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.

Keywords: silica sulphuric acid (SSA) – heterogeneous catalyst – thioacetalisation – chemoselectivity – carbonyl compounds – 1,2-ethanedithiol

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0443-4

Chemical Papers 68 (3) 417–421 (2014)