Camps, P;
Lozano, D;
Barbaraci, C;
Font-Bardia, M;
Javier Luque, F;
Estarellas, C;
(2018)
Generation and Reactions of an Octacyclic Hindered Pyramidalized Alkene.
The Journal of Organic Chemistry
, 83
(10)
pp. 5420-5430.
10.1021/acs.joc.8b00212.
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Abstract
Octacyclo[10.6.1.01,10.03,7.04,9.08,19.011,16.013,17]nonadeca-5,8,14-triene (27), a hindered pyramidalized alkene, has been generated from a diiodide precursor. Contrary to the usual behavior of known pyramidalized alkenes, no Diels–Alder adducts were obtained from the present alkene when it was generated by different standard procedures in the presence of different dienes. However, products derived from the reduction, t-BuLi addition, condensation with the solvent, or dimerization were isolated from these reactions, depending on the conditions used to generate it. No [2 + 2] cross product among this pyramidalized alkene and tricyclo[3.3.1.03,7]non-3(7)-ene was formed when a mixture of the corresponding precursor diiodides was reacted with sodium amalgam. The analysis of selected geometrical and orbital parameters determined from quantum mechanical calculations indicates that the degree of pyramidalization of this alkene and its higher steric hindrance compared with other polycyclic pyramidalized alkenes may explain its peculiar reactivity.
| Type: | Article |
|---|---|
| Title: | Generation and Reactions of an Octacyclic Hindered Pyramidalized Alkene |
| Open access status: | An open access version is available from UCL Discovery |
| DOI: | 10.1021/acs.joc.8b00212 |
| Publisher version: | https://doi.org/10.1021/acs.joc.8b00212 |
| Language: | English |
| Additional information: | This version is the author accepted manuscript. For information on re-use, please refer to the publisher’s terms and conditions. |
| UCL classification: | UCL UCL > Provost and Vice Provost Offices > UCL BEAMS UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences UCL > Provost and Vice Provost Offices > UCL BEAMS > Faculty of Maths and Physical Sciences > Dept of Chemistry |
| URI: | https://discovery-pp.ucl.ac.uk/id/eprint/10062134 |
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