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Updated: May 27, 2026

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
1-Phenyl-5-{[2-(trimethyl-sil-yl)eth-yl]sulfon-yl}-1H-tetra-zole
David Tymann1, Björn Nelson, Carsten Strohmann
1Fakultät Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany.
Abstract:
The title compound, C(12)H(18)N(4)O(2)SSi, was synthesized to be employed in a Julia-Kocieński olefination. In the mol-ecule, the dihedral angle between the phenyl ring and the tetra-zole ring is 41.50 (5)°. The significantly longer Si-C(methyl-ene) bond [1.8786 (13) Å] and the shortened adjacent C-C bond [1.5172 (18) Å], as well as the significant deviation of the corresponding Si-C-C angle [114.16 (9)°] from the ideal tetra-hedral angle, can be attributed to the β-effect of silicon. In the crystal, mol-ecules are held together by van der Waals inter-actions.
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