Structural Chemistry

, Volume 17, Issue 4, pp 419–422

Tetra-tert-butylethylene, fantasy, fake, or reality?

Authors

  • Dieter Lenoir
    • GSF-Research Center NeuherbergInstitute of Ecological Chemistry, Postfach 1129
  • Carsten Wattenbach
    • GSF-Research Center NeuherbergInstitute of Ecological Chemistry, Postfach 1129
    • Department of Chemistry and BiochemistryUniversity of Maryland, Baltimore County
Original Paper

DOI: 10.1007/s11224-006-9061-x

Cite this article as:
Lenoir, D., Wattenbach, C. & Liebman, J.F. Struct Chem (2006) 17: 419. doi:10.1007/s11224-006-9061-x

Abstract

This paper reviews all recent attempts to prepare tetra-tert-butylethylene. Some of the synthetic pathways approached this molecule very close but failed during the last step. According to recent DFT calculations this alkene should be a stable molecule with a strain energy in the range of 93 kcal/mol. Since all synthetic approaches failed new methodologies have to be developed, that is either synthesis of the perfluoro derivative of this alkene or the reaction of the radical cation or the radical anion of di-tert-butylmethane with the carbene by a crossed beam technique in the gas phase.

Keywords

Sterically strained alkenesTetra-tert-butylethyleneHighly twisted ethylenesDFT calculations

Abbreviation

(1)

Tetra-tert-butylethylene

(2)

Di-tert-butyldiisopropylpropylethylene

(3)

Tri-tert-butylethylethylene

(4)

Tetraaldehyde

(5)

Di-tert-butylcarbene

(6)

anti-fenchylidenefenchane

(7)

1,2-Di-tert-butyl-3,3,5,5-tetramethylcyclopentene

(8)

Tetra-tert-butylethane

(9)

1,1-Dimethyl-2-tert-butylcyclopropane

Copyright information

© Springer Science+Business Media, Inc. 2006