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Reductive metalation of 1,2-diaryl-substituted ethenes: synthetic applications

Ugo Azzena*, Giovanna Dettori, Caterina Lubinu, Alberto Mannu and Luisa Pisano

*Dipartimento di Chimica, UniversitÓ di Sassari, via Vienna 2, I-07100 Sassari, Italy, Email:

U. Azzena, G. Dettori, C. Lubinu, A. Mannu, L. Pisano, Tetrahedron, 2005, 61, 8663-8668.

DOI: 10.1016/j.tet.2005.06.108

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Reduction of stilbenes with Na metal in dry THF allowed easy access to various 1,2-diaryl-1,2-disodiumethanes. These diorganometallic intermediates gave 1,2-diarylethanes upon aqueous work up, or trans-1,2-diaryl-substituted cyclopentanes by cycloalkylation with 1,3-dichloropropanes.

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Key Words

Dicarbanions, Stilbenes, Metalation, Reduction, Cycloalkylation, Cyclopentanes, Sodium

ID: J72-Y2005-3050