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Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Química Orgánica I, Unidad Asociada al CSIC, Facultad de Química, Universidad Complutense de Madrid, 28040-Madrid, Spain
E-mail: alcaideb@quim.ucm.es
; Fax: +34-91-3944103
b
Instituto de Química Orgánica General, IQOG, Consejo Superior de Investigaciones Científicas (CSIC), Juan de la Cierva 3, 28006-Madrid, Spain
E-mail: Palmendros@iqog.csic.es
; Fax: +34-91-5644853
Org. Biomol. Chem., 2012,10, 7603-7609
DOI:
10.1039/C2OB26085A
Received
05 Jun 2012,
Accepted
03 Aug 2012
First published online
03 Aug 2012
A stereoselective synthesis of 1-substituted (E)-2-aryl-but-1-en-3-ynes, including tetrasubstituted alkenes, has been developed from aryl-substituted α-allenols by treatment with the AcCl–NaOH (aqueous) system. This transformation might be explained through the elimination of acetic acid, made up of a δ-hydrogen and the acetate group in the initially formed α-allenic acetate.
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Organic & Biomolecular Chemistry
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