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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Generation and reactions of two new functionalized tricyclo[ 3,7]oct-1(5)-ene derivatives.

The generation of the new functionalized and highly pyramidalized alkenes, 3,7-(2,2'-biphenylene)tricyclo[,7)]oct-1(5)-ene (20) and 3,7-sulfonyldioxytricyclo[,7)]oct-1(5)-ene (39), and their trapping with 1,3-diphenylisobenzofuran and 11,12-dimethylene-9,10-dihydro-9,10-ethanoanthracene are described. While both alkenes 20 and 39 failed to give the expected cyclobutane or diene dimers, 20 was reacted with 3,7-dimethyltricyclo[,7)]oct-1(5)-ene (1b) to give the cross-coupled product 4,5-(2,2')-biphenylene-10,11-dimethylpentacyclo[,5).1(4,7).1(8,11)]hexadeca-1,7-diene (33). DFT calculations [B3LYP/6-31G(d)] on compound 20 gave important parameters of this pyramidalized alkene, such as the pyramidalization angle (61.7 degrees), the strain energy (72.9 kcal/ mol), and the HOMO/LUMO gap (3.79 eV).[1]


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