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Synlett 1997; 1997(6): 681-682
DOI: 10.1055/s-1997-3240
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Unusually High Reactivity of the C-Si Bond in the Lewis Acid Mediated Reactions of (E)-1-(Trimethylsilyl)-2-(isopropylthio)ethylene with Carbonyl Electrophiles

Bianca F. Bonini, Mauro Comes-Franchini, Mariafrancesca Fochi, Germana Mazzanti, Alfredo Ricci*
  • *Dipartimento di Chimica Organica “A. Mangini”, Univesità di Bologna, Viale Risorgimento 4, I-40124-Bologna (Italy), Fax +39 51 6443654; E-mail: ricci@ms.fci.unibo.it
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Publication History

Publication Date:
31 December 2000 (online)

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In the reaction with benzaldehyde and with cyclic α,β-unsaturated ketones in the presence of Lewis acids (E)-1-(trimethylsilyl)-2-(isopropylthio)ethylene exhibits enhanced reactivity compared to that of (E)-1-(trimethylsilyl)-hept-1-ene. Moreover depending upon the nature of the Lewis acid used, stoichiometric or catalytic pathways can be envisioned which lead to different reaction products.

vinylsilanes - Lewis acids - carbonyl groups - substitution

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