Seemingly Impossible Organic problem

[Guest Red Lemon]

Hey guys, I've been given a synthesis problem that I just cannot solve. It says: "Outline a strategy which might be used to give the interlocking alkene complex shown below from two molecules of a large cyclic monoalkene."

 

The interlocking complex appears to be a catenane with the two rings just looped through each other. The large cyclic alkene is just a huge (unspecified size) ring with nothing but one alkene group and the rest just CH2 groups.

 

Any ideas?

[budullewraagh]

i'll make an attempt, but truth be told, i have never tried this and know little of catenanes and such.

 

first, you could add a carbene halide to form the cyclic ring. also you could halogenate the ends of your hydrocarbons and react with Na, Mg, or Zn, etc, forming a cyclic ring. of course, you have to interlink the two rings, which is the hard part.

 

you should play around with polarity; add a nucleophile to the center of one ring, form a carbonium cation with the other, cleave the link you make between the two, create dipole attractions with the ends of one of the rings.