The synthesis of rigid norbornylogs for the purpose of studying orbital interactions through bonds
1986; Elsevier BV; Volume: 42; Issue: 6 Linguagem: Inglês
10.1016/s0040-4020(01)87597-9
ISSN1464-5416
AutoresMichael N. Paddon‐Row, Evangelo Cotsaris, Harish K. Patney,
Tópico(s)Bioactive Compounds and Antitumor Agents
ResumoThe synthesis of members of the series of rigid bichromophoric norbornylogs 4–8 is described. Dienes 4a and b were synthesized according to Scheme 1. Reductive decolorination of 26–28(Scheme 2) gave dienes 5b-d, respectively. Benzene annelation of the appropriate ene substrate, using tetrachlorodimethoxy-cyclopentadiene, as outlined in Scheme 3, gave the dibenzo compounds 6a-c. The dibromoquinodimethane intermediate 49 was trapped by the appropriate diene to give the bisnaphtho compounds 7a-c. The extended norbornylogs 8a and b were synthesized using a combination of metal catalyzed (2+2) cycloaddition of DMAD and (2+2+2)cydoaddition of quadricyclane to ene substrates(Scheme).The photoelectron spectra of some of the dienes are discussed in terms of through bond orbital interactions.
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