Ring Tension, Hydrocarbon Acidity, and New «Super-Bases»

Authors

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

DOI:

https://doi.org/10.2533/chimia.1986.306

Abstract

Addition of disodium pinacolate or, particularly, potassium tert-butoxide considerably increases the transmetalating power of pentylsodium. A hexane slurry of such «NACNAOR» or «NACKOR» reagent mixtures readily and selectively converts 3,3-dimenthyl-1-butene, camphene, bicyclo[2.2.2]oct-2-ene, and spiro[4.4]nona-1,3-diene into sodio derivatives. The metalation of cyclopropanes such as nortricyclane, norcarane or bicyclo[2.1.0]pentane («housane») proved to be possible too, although the yields were less satisfactory. On the other hand, cyclobutanes were found to be virtually inert towards alcoholate-activated pentylsodium.

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Published

1986-09-30

Issue

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

Section

Articles

License

Copyright (c) 1986 Manfred Schlosser

Creative Commons License

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

How to Cite

[1]
M. Schlosser, J. Hartmann, M. Stähle, J. Kramař, A. Walde, A. Mordini, Chimia 1986, 40, 306, DOI: 10.2533/chimia.1986.306.