Cookies Policy

This site uses cookies. By continuing to browse the site you are agreeing to our use of cookies.

I accept this policy

Find out more here

Isomerisation of Decatetraenes and Dimethyldecatetraenes Via Pentadienyl and 3-Methylpentadienyl Radicals

No metrics data to plot.
The attempt to load metrics for this article has failed.
The attempt to plot a graph for these metrics has failed.
The full text of this article is not currently available.

Brill’s MyBook program is exclusively available on BrillOnline Books and Journals. Students and scholars affiliated with an institution that has purchased a Brill E-Book on the BrillOnline platform automatically have access to the MyBook option for the title(s) acquired by the Library. Brill MyBook is a print-on-demand paperback copy which is sold at a favorably uniform low price.

This Article is currently unavailable for purchase.
Add to Favorites
You must be logged in to use this functionality

Cover image Placeholder

The thermal isomerisations of E,E-deca-1,3,7,9-tetraene and E,E-3,7-dimethyldeca-1,3,7,9-tetraene take place via the intermediacy of pentadienyl and 3-methylpentadienyl radicals, respectively, rather than by concerted Cope type rearrangements. The pentadienyl radicals isomerise to pairs of E- and Z-pentadienyl radicals which recombine by end to end and end to centre, but not centre to centre, coupling to give mixtures of isomeric decatetraenes. The relative free energies of formation of these decatetraenes were derived from their equilibrium proportions and compared with relative enthalpies of formation calculated by the empirical MM2(87) method and the semi-empirical AM1 and PM3 SCF MO methods. None of these theories was successful at predicting and rationalizing the experimentally observed enthalpy changes. However, they all were somewhat better in dealing with branching than with cis/trans isomerisation. Frontal strain in the decatetraene plays an important part in influencing their stability.

Affiliations: 1: Department of Chemistry, University of St. Andrews, St. Andrews, Fife KY16 9ST, UK; 2: Steacie Institute for Molecular Sciences, National Research Council of Canada, Ottawa, Canada KIA OR6


Full text loading...


Data & Media loading...

Article metrics loading...



Can't access your account?
  • Key

  • Full access
  • Open Access
  • Partial/No accessInformation