Highly pyramidalized tricyclo[3.3.0.03,7]oct-1(5)-ene and related compounds: High-level ab initio study, synthesis and trapping of tetracyclo[5.2.1.02,6.03,8] dec-7-ene, and cross-coupling reactions
1998; Elsevier BV; Volume: 54; Issue: 18 Linguagem: Inglês
10.1016/s0040-4020(98)00185-9
ISSN1464-5416
AutoresPelayo Camps, Mercé Font‐Bardía, N. Quirós Méndez, Francesc Pérez, Xavier Pujol, Xavier Soláns, Santiago Vázquez, Montserrat Roca vilalta,
Tópico(s)Photochemistry and Electron Transfer Studies
ResumoThe geometries, olefin strain energies, heats of hydrogenation and relative HOMO/LUMO energies of tricyclo [3.3.0.03,7]oct-1(5)-ene and related compounds have been obtained by ab initio calculations using different basis sets. Tetracyclo-[5.2.1.02,6.03,8]dec-7-ene, a new member of this series of highly pyramidalized alkenes, has been generated and trapped as different Diels-Alder adducts; in the absence of a trapping agent, it gives the expected dimeric derivatives in a non-stereoselective way and in low yield. For the first time, good yield cross-coupling reactions among highly pyramidalized alkenes have been carried out. The structure of a tetrasecododecahedrane diepoxide derived from a cross-coupled product has been established by X-Ray diffraction analysis.
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