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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 18
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Original Articles

A Facile Synthesis of α-Phenylchalcogeno(S, Se) α,β-Unsaturated Esters from Ethyl α-Bromo-α-phenylchalcogeno Acetates

C. C. Silveira Departamento de Química, Universidade Federal de Santa Maria, 97.105–900, Santa Maria, RS, Brazil
,
C. S. Botega Departamento de Química, Universidade Federal de Santa Maria, 97.105–900, Santa Maria, RS, Brazil
,
C. R. B. Rhoden Departamento de Química, Universidade Federal de Santa Maria, 97.105–900, Santa Maria, RS, Brazil
,
M. R. S. Nunes Departamento de Química, Universidade Federal de Santa Maria, 97.105–900, Santa Maria, RS, Brazil
,
A. L. Braga Departamento de Química, Universidade Federal de Santa Maria, 97.105–900, Santa Maria, RS, Brazil
&
E. J. Lenardão D. Quim. Anal. Inorg[acaron]nica, Universidade Federal de Pelotas, Pelotas, RS, Brazil
Pages 3371-3380 | Received 30 Mar 1998, Published online: 22 Aug 2006
 
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Abstract

Ethyl α-bromo-α-phenylseleno acetate 1 and ethyl α-bromo-α-phenylthio acetate 2 react with aldehydes in the presence of dibutyltelluride to give α-phenylchalcogeno-α,β-unsaturated esters, with Z preferential stereochemistry.

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