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Synlett 2001; 2001(4): 0458-0466
DOI: 10.1055/s-2001-12310
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The Preparation of Mono-, 1,1-Di-, trans-1,2-Di- and Trisubstituted Ethylenes by Benzotriazole Methodology

Alan R. Katritzky* , Dorin Toader
  • *Center of Heterocyclic Compounds, University of Florida, Gainesville, FL 32601-7200, USA; Fax + (352)3 92 91 99; E-mail: katritzky@chem.ufl.edu
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Publication Date:
31 December 2001 (online)

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Mono- and 1,1-disubstituted ethylenes are available by vicinal elimination of benzotriazolyl and trimethylsilyl groups from readily available intermediates of type BtCRR′·CH2SiMe3 (Bt = benzotriazol-1-yl). Low-valent Ti compounds cause vicinal elimination of benzotriazolyl and hydroxyl groups from both diastereoisomers of RCHBt·CHR·OH compounds to give styrenes and dienes with high trans-stereoselectivity: the starting materials are easily obtained from Bt-stabilized carbanions and aldehydes.

olefins - organosilicon - low-valent titanium - dienes - vicinal elimination