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Synthesis 2011(8): 1233-1242  
DOI: 10.1055/s-0030-1259969
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© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (Diphenylphosphinoyl)methyl Vinyl Sulfides, Symmetric and Asymmetric Divinyl Sulfides from Bis[(diphenylphosphinoyl)methyl] Sulfide

Claudio C. Silveira*a, Francieli Rinaldia, Mariana M. Bassacoa, Rafael C. Guadagninb, Teodoro S. Kaufmanc
a Departamento de Química, Universidade Federal de Santa Maria, 97105.900, Santa Maria, RS, Brazil
Fax: +55(55)32208754; e-Mail: silveira@quimica.ufsm.br;
b Departamento de Ciências Exatas e da Terra, Universidade Federal de São Paulo, 09971.270, Diadema, SP, Brazil
c Instituto de Química Rosario (IQUIR, CONICET-UNR), Suipacha 531, S2002 LRK Rosario, Argentina
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Publication History

Received 28 December 2010
Publication Date:
24 March 2011 (online)

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Abstract

Convenient Horner-Wittig-based synthetic approaches to the preparation of (diphenylphosphinoyl)methyl vinyl sulfides as well as symmetrically and unsymmetrically substituted divinyl sulfides, are described. The syntheses involve the use of the easily available bis[(diphenylphosphinoyl)methyl] sulfide as a common starting material and sodium hydride as base, in tetrahydrofuran.

Key words

sulfur - Wittig reaction - alkenation - ketones - aldehydes

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