[legoart]

Hello,

I was wondering how to do the following reaction -

Cycloheptanol  + LiAlH₄/TiCl₄ ----> ?

I feel like the reaction would simply lead to cycloheptane - but I'm really not sure and the reagents are really confusing me (in terms of how they would react with the hydroxyl group) Any help would be greatly appreciated!

Thank you! 

[fledarmus]

Perhaps this would help?

http://en.wikipedia.org/wiki/McMurry_reaction

[Mitch]

But, it is an alcohol not a ketone?

[wengforever]

in my opinion, TiCl4 would chelate with the hydroxy group to give a -OTiCl3, which can be seemed as a leaving group and attacked by a hydrogen anion form LiAlH4

[spirochete]

To Weng: I don't think LiAlH4 can do SN2 reactions.  It's my understanding that only super hydride (another more reactive hydride delivery reagent) can do SN2.  Maybe if you heat the crap out of it an SN1 type reaction could happen?  This would give cycloheptane as a product.

Maybe some form of reduced titanium could abstract a hydrogen from the alcohol in a radical reaction, leading to a common intermediate from the McMurry reaction?  I would do some research on the McMurry reaction of alcohols if you really want to know, to see if alcohols are a potential substrate.  In this case you'd get a dimerized alkene product.