Structural Chemistry

, Volume 17, Issue 4, pp 419–422 | Cite as

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

  • Dieter Lenoir
  • Carsten Wattenbach
  • Joel F. Liebman
Original Paper

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 alkenes Tetra-tert-butylethylene Highly twisted ethylenes DFT 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

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Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • Dieter Lenoir
    • 1
  • Carsten Wattenbach
    • 1
  • Joel F. Liebman
    • 2
  1. 1.GSF-Research Center NeuherbergInstitute of Ecological Chemistry, Postfach 1129NeuherbergGermany
  2. 2.Department of Chemistry and BiochemistryUniversity of Maryland, Baltimore CountyBaltimoreUSA

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