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Synthesis 2005(20): 3639-3643  
DOI: 10.1055/s-2005-918450
PAPER
© Georg Thieme Verlag Stuttgart · New York

Sequential Reduction and Dehydration of Phenacyl-(E)-Styryl Sulfones to Unsymmetrical (E,E)-Bis(styryl) Sulfones

Muralidhar Reddy Mallireddigari, Venkat R. Pallela, E. Premkumar Reddy, M. V. Ramana Reddy*
Fels Institute for Cancer Research, Temple University School of Medicine, 3307 North Broad Street, Philadelphia, PA 19140-5101, USA
Fax: +1(215)7071454; e-Mail: rreddy@temple.edu;
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Publication History

Received 27 January 2005
Publication Date:
27 October 2005 (online)

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Abstract

β-Keto vinylic sulfones, the key building blocks for the synthesis of the title compounds, were prepared by two different routes. NaBH4 reduction of these compounds afforded β-hydroxy vinylic sulfones which were dehydrated with acetic anhydride and BF3·Et2O to obtain bis(styryl) sulfones. Alternatively, one-pot synthesis of these bis(styryl) sulfones was also achieved directly from β-keto vinylic sulfones by treating with NaBH4 in EtOH followed by refluxing with concentrated HCl.

Key words

β-keto vinylic sulfones - β-hydroxy-(E)-vinylic sulfones - (E,E)-bis(styryl) sulfones - styrylsulfinate - Knoevenagel condensation

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