Synthesize 1,5-diazocane using only benzene as a source of carbon atoms, and ammonia as the only source of nitrogen atoms.
My attempt: Noticing that the target compound has split the benzene ring, I attempted to split the benzene ring as well. I thought of two options:
H2/Pt at high temperature and pressue
Creation of phenol and subsequent oxidation
As the first process would create cyclohexane and be difficult to manipulate, I went with the second option. To synthesize phenol from benzene, I used a nitration, followed by reduction to create aniline, then used nitrous acid to create the benzenediazonium salt, and decomposed the salt in the presence of water to create phenol. After the oxidation of phenol I got 1,4-benzoquinone.
Now, realizing that I would need to create 1,3-propandial in order to use $\ce{NH3/NaBH3CN}$ to create 1,5-diazocane, I attempted to make 1,3-propandial from 1,4-benzoquinone. Ozonolysis of 1,4-benzoquinone produces 2-oxo,1,3-propandial, which has an extra carbonyl group. Because of the many carbonyl groups involved in this compound, I was thinking of removing the carbonyl groups directly from benzoquinone, and doing an ozonelysis from there. However, I was not sure if any standard carbonyl reactions, such as the Wolff-Krishner or the Clemmensen reaction could be applied to remove the carbonyls, seeing as they are heavily resonance stabilized.
Therefore, I was wondering if these reactions do proceed on benzoquinone, and if not, then what other plausible ways of synthesizing 1,5-diazocane exist?