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Convenient method to obtain homoallylic thioethers from aromatic dithioacetal derivatives

Natalia Buszta, Wojciech J. Depa, Agata Bajek, and Grażyna Groszek

Rzeszów University of Technology, Rzeszow, Poland

 

E-mail: ggroszek@prz.edu.pl

Abstract: A new, convenient, and efficient method for the synthesis of homoallylic aromatic thioethers was developed. The present method consists of the formation of arylthionium intermediates from aromatic dithioacetals, which are trapped by a π-nucleophile. Screening of diverse aromatic substrates, selected Lewis acids, and allylstannane and allylsilane were evaluated. The method was found suitable for the preparation of homoallylic aryl thioethers bearing electron donating o- and p-groups only, as substrates with electron withdrawing groups were found unreactive to this system.

Keywords: Aromatic dithioacetals ; Allylation ; Lewis acid ; Homoallyl sulfides 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-019-00837-3

 

Chemical Papers 73 (11) 2885–2888 (2019)

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