Converting cyclic compounds to their corresponding aliphatic compounds
The reaction you want to know about is "Cleavage reaction" in particular oxidative cleavage.

In this dihydroxylation, if the solution is warm or acidic or too concentrated, oxidative cleavage of the glycol may occur.

Then they can be reduced to aldehydes by reducing agents.Reduction of carboxylic acids to aldehydes is difficult because aldehydes are more reactive than carboxylic acids toward most reducing agents. Almost any reagent that reduces acids to aldehydes also reduces aldehydes to primary alcohols.  

Lithium tri-tert-butoxyaluminum hydride, LiAlH(O-t-Bu)3 is a weaker reducing agent than lithium aluminum hydride. It reduces acid chlorides to aldehydes because acid chlorides are strongly activated toward nucleophilic addition of a hydride ion.

Under these conditions, the aldehyde reduces more slowly and can be isolated. Therefore, reduction of an acid to an aldehyde is a two-step process: Convert the acid to the acid chloride, then reduce using lithium tri-tert-butoxyaluminum hydride.





And now we can reduce it by the Wolff Kishner reduction. 


Ethylene glycol, diethylene glycol, or another high-boiling solvent is used to facilitate the high temperature (140–200 °C) needed in the second step. I am assuming you can convert the cyclohexane to cyclohexene by any radical halogenation and then dehydrohalogenation.