# Dimethylene Cyclohexane to Octalin-1,4-Dione | Hydroboration vs. Ozonolysis Pros Cons

With regards to the following synthesis, what are some pros and cons of using hydroboration oxidation followed by oxidation of the alcohols compared to ozonolysis.

More specifically, how do the two compare as to yields of the final product, cost / amount of reagents, speed of reactions, unwanted side reactions?

Here is the synthesis, along with the two ways to prepare the cyclohexadione:

• You lost some carbon atoms in your hydroboration. – Zhe Mar 1 '17 at 23:25
• What Zhe said. Of your two approaches, only one works. Now, there are other oxidative cleavage methods... – Ben Norris Mar 2 '17 at 3:17
• It's not part of your question, but your last line won't work. Alpha bominate carbonyl compounds using $\ce{Br2}$ in acetic acid. You need a base to eliminate the halide, not sulfuric acid. – Ben Norris Mar 2 '17 at 3:30

Now, you may be able to take the carbocylic acid, covert to acid halide and then react with $\ce{LiCuMe2}$ to get the ketone, which should undergo Baeyer-Villager oxidation followed by hydrolysis to give the alcohol you want. Or you could covert the diacid to the diamide and subject it to Hofmann degradation to get the amines, which you might be able to convert to the diazo salt with HONO, which may hydrolyze to give the desired diol. Both routes ae significantly more convoluted than ozonolysis, which decreases oveall yield and increases cost.