57015-35-7Relevant articles and documents
Tetra- and Pentacyclic Tricyclo2,7>hept-3-ene Derivatives; Trapping Products of Tricyclo2,7>hepta-3,4-diene
Christl, Manfred,Lang, Reinhard,Lechner, Monika
, p. 980 - 996 (2007/10/02)
Reaction of 7,7-dibromotetracyclo2,4.03,5>heptane (4) with methyllithium generates tricyclo2,7>hepta-3,4-diene (7) as a reactive intermediate having diradical character, which either polymerizes or is trapped by suitable reagents such as styrene, 1,1-diphenylethene, butadiene, cyclopentadiene, furan, 1,3-cyclohexadiene, and cycloheptatriene.The products are the tetra- or pentacyclic compounds 8-10 and 12-14, 17, respectively, and contain the tricyclo2,7>hept-3-ene system.Unequivocal evidence concerning the structure of these products follows from the 13C-NMR spectra.While butadiene and 7 form a 1,2-adduct, the vinylcyclobutane derivative 10, cyclic 1,3-dienes provide 1,4-adducts, which presumably do not ensure from a one step process, but are the result of the collapse of a diradical intermediate. - The double bonds of 8 and 13 can be hydrogenated by means of diimine.Dibromcarbene adds to the double bond of 8 to give the spirohexane derivative 25.