[AlphaScent]

What do you think of reducing 2 triple bond to 2 trans double bonds using sodium in liquid ammonia as your conditions.


See attached for scheme.

Cheers!

[discodermolide]

There was a very recent paper by Fürstner on this topic
A Functional-Group-Tolerant Catalytic trans Hydrogenation of Alkynes**
Karin Radkowski, Basker Sundararaju, and Alois Fürstner*
In Angewandte Chemie English.
DOI: 10.1002/anie.201205946
2012 vol. 52 (1) pp. 355-360

[AlphaScent]

Thanks Disco,

I cannot access that paper.  Was it to be a link?  I do not have the ability to access most publications.  My company does not spring for such luxuries.

Can you email it to me if you do not want to post?  I can PM you if you'd like?

Thanks again,

Cheers

[mjpam]

While I'm sure that the resource that disco provider for you will be invaluable, you might want to examine the reaction of alcohols, particularly with akali metals (group 1 elements) that are covered in a first course in organic chemistry. Consider, for instance, how you might deprotonate an alcohol in a nonpolar solvent and also what your chosen solvent system is.

The latter is not something, honestly, even occurred to me until I started writing this response, nor is it something that I have seen covered in standard introductory organic textbooks. (I learned about it by reading my inorganic chemistry textbook after I had graduated.)

ETA: disco's citation is available in free full-text. Google Scholar can sometimes be helpful in finding free text if you check the All <x> versions avaible link or by clicking the Cited by <x> link after googling the title and then clicking on the article title when you are taken to the Google Scholar citation page.

[AlphaScent]

Yea M I should have considered before putting the scheme up.  The alcohol I am not too worried about, like williamson ether or anything taking place.  Though there would be any halides floating around.  I do see what you are getting at.  Doing sodium in liquid ammonia is the SOP for making trans bonds around here.  Though you did get me thinking about maybe lithium in THF is also a viable option for me. 

What I was really stressing is the reduction of the polyolefin.  Has anyone done it using basic reduction conditions i.e. without really expensive catalysts.

Thanks though for your input.

I did indeed find the paper on google once i looked a bit harder.  Thank you again.

The paper details ruthenium catalysts for hydrogenation.  Good read!!

Cheers!!