Acidity Enhancement through Homoconjugation: Selective Introduction of Sodium into Olefinic Positions

Authors

  • Manfred Stähle Institut de Chimie organique de l’Université Rue de la Barre 2, CH-1005 Lausanne
  • Ruth Lehmann Institut de Chimie organique de l’Université Rue de la Barre 2, CH-1005 Lausanne
  • Jaroslav Kramař 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.1985.229

Abstract

When treated with butyllithium and sodium tert-butoxide, both norbornadiene and norbornene undergo a hydrogen/sodium-exchange at the 2-position. The diene, however, reacts approximately 30 times faster. Bicyclo[3.2.0]hepta-2,6-diene is also more readily metalated than bicyclo[3.2.0]hept-6-ene and its 7-position is preferentially attacked. Finally, cycloheptatriene is smoothly converted into 2-cycloheptatrienylsodium.

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Published

1985-08-31

Issue

Vol. 39 No. 7-8 (1985): Forschung/Research

Section

Articles

License

Copyright (c) 1985 Manfred Stähle

Creative Commons License

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

How to Cite

[1]
M. Stähle, R. Lehmann, J. Kramař, M. Schlosser, Chimia 1985, 39, 229, DOI: 10.2533/chimia.1985.229.