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Vinylic Substitutions Promoted by PhSeZnCl: Synthetic and Theoretical Investigations
Author(s) -
Santoro Stefano,
Battistelli Benedetta,
Testaferri Lorenzo,
Tiecco Marcello,
Santi Claudio
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900800
Subject(s) - chemistry , stereospecificity , alkene , ketone , nucleophile , nucleophilic substitution , zinc , halide , sn1 reaction , medicinal chemistry , reaction mechanism , atom (system on chip) , stereochemistry , computational chemistry , organic chemistry , catalysis , computer science , embedded system
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 β‐chloro‐α,β‐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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)