Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 29, Pages 4921-4925Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900800
Keywords
Selenium; Zinc; Vinylic substitution; Nucleophilic substitution; DFT calculations
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Funding
- M.I.U.R. (Ministero Italiano Universita e Ricerca)
- Progetto di Ricerca d'Interesse Nazionale [PRIN2007]
- Consorzio CINMPIS
- Bari and University of Perugia
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Vinyl selenides can be easily obtained through nucleophilic substitution of the corresponding halides by using PhSeZnCl in THF as well as on water conditions. The reaction is stereospecific with retention of the alkene geometry. The only exception has been observed in the reaction conducted on a beta-chloro-alpha,beta-unsaturated ketone, which afforded the (Z) product starting from either the (E) or (Z) isomer. DFT calculations have been performed in order to investigate the reaction mechanism, the stereochemistry of the process and the role of the zinc atom. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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