Bicyclo compounds Norbomadiene

Heterosubstitution at nonactivated positions is also possible by using highly reactive metalating agents such as pentylsodium. When used in the presence of tm-BuOK, it readily and selectively forms vinylsodium derivatives that can subsequently be converted to organosilicium compounds.243 Norbomadiene and bicyclo-[3.2.0]hepta-2,6-diene are also readily silylated via the corresponding sodium compounds formed in the reaction with BuLi-rm-BuONa.244 Similar transforma-tions of strained polycyclic cyclopropanes were also achieved [Eq. (10.45) ] ... 

As shown in Table 6 and Figure 1, the oxidation potentials of 2-substituted norbomadienes (1), 2-substituted bicyclo[2.2.2]octa-2,5-dienes (2) and 4-substituted [2.2]paracyclophanes (3) clearly indicate that the transannular interaction between two double bonds contributes already at the stage of the first electron transfer. Namely, in compounds 1-3, the electron is transferred from the unsaturated bond which is not substituted by the electron-withdrawing group, Figure 1 shows the... 

This compound has been prepared by the reaction of sodium tetrachloro-palladate and the olefin or by the displacement of carbon monoxide firom [COPdQ2L or benzonitrile from (CeH,C N)2PdQ2. Bicydo[2.2.1]hepta-2,5-diene (2,S-norbomadiene) may be substituted in the following procedure for l,S-cyclooctadiene to yield (bicyclo[2.2.1]hepta-2,S-diene)dichloro-palladium(II). 

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