[Kevsta]

I was wondering if 3-Methylenecyclohexene with BH3 * THF and H2O2, NaOH (Hydroboronation oxidation) would create 3-(methanol)-1-cyclohexene? I was wondering if the hydroboronation would do anything with the alkene in the cyclohexene instead of the less substituted.

[discodermolide]

I would expect both C=C to react and you will get a mixture of products.

[Kevsta]

So, here is my synthesis problem: cyclohexane to 3-(2,2-dimethylpropanol)-cyclohexene.  Here are the steps I have done so far:
1. Br2, hv
2. NaOH
3. Na2Cr2O7,H2SO4,H2O
4. MeMgBr,H2O
5. H2SO4, Heat
6. HBr, ROOR
7. t-ButOK
8. Br2, hv
9. t-butOk
10. BH3*THF, H2O2, NaOH
11. PCC, CHCl2
12. tertbutyl-MgBr (Gignard rection)

So should I turn that pi bond in the cyclohexene into a OH and protect it and then deprotect it after?

[discodermolide]

you going to use 12 steps or are these the reagents you have to choose from?

[Kevsta]

These are reagents I chose to do this reaction.

[discodermolide]

So how far have you got?
Let's see what you have achieved thus far.

[Kevsta]

Huh?  What do you mean?  The question asked for the reagents necessary to perform the reaction and I used those 12, however when I do the hydroboronation with the 3-Methylenecyclohexene in step 10, you mentioned a mixture of products would be formed, so I was wondering how I would work around that.

[discodermolide]

I think you have to show the individual steps and individual reagents you would use to carry them out. you will then have to eliminate H₂O to regenerate the double bond.
Sorry it was not quite clear to me what was going on with this question. I guess I am still asleep.

[Kevsta]

Here..

So are you saying when the Hydroboronation oxidation takes place, the resulting compound has no alkenes and has two alchohols?  and then at the end I would eliminate?

[discodermolide]

That scheme looks OK.

[Kevsta]

Wait, i'm confused now.  So the hydroboronation wont create a mixture of products like you said in the beginning?

[discodermolide]

Yes I think it will. But for the purposes of your exercise forget it.

[Kevsta]

Alright, thanks!

[curiouscat]

In the step with Br2 and hν how come the Br2 doesn't add on to the double bond in the ring?

[Kevsta]

A radical on an sp2 is really unstable.