Metalation of Olefinic Positions in Norbornadiene: Enhancement and Attenuation of Kinetic CH-Acidities by a Neighboring Enesilane Moiety

Authors

  • Alessandro Mordini Institut de Chimie organique de l’Université Rue de la Barre 2, CH-1005 Lausanne
  • Manfred Schlosser Institut de Chimie organique de l’Université Rue de la Barre 2, CH-1005 Lausanne

DOI:

https://doi.org/10.2533/chimia.1986.309

Abstract

When treated with butyllithium in the presence of sodium or potassium tert-butoxide, 2-trimethylsilyl- and 2-triethylsilyl-norbornadiene undergo hydrogen/metal-exchange mainly at the 5-position. The latter position is found to be slightly activated relative to unsubstituted norbornadiene while the two other olefinic positions prove to be quite inert. Two side reactions are observed: the metalation of silicon-attached methyl groups and the replacement of the entire trialkylsilyl group by a metal atom.

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Published

1986-09-30

Issue

Vol. 40 No. 9 (1986): Forschung/Research

Section

Articles

License

Copyright (c) 1986 Alessandro Mordini

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
A. Mordini, M. Schlosser, Chimia 1986, 40, 309, DOI: 10.2533/chimia.1986.309.