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Topic: Name of compound?  (Read 1915 times)

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Offline AlphaScent

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Name of compound?
« on: January 02, 2015, 02:21:48 PM »
Another question I am looking at is how this compound attached is used to make double bonds.  You treat it with KHMDS and then an aldeyde.  A E double bond is then formed.  I assume this has to be a wittig type mechanism with sulfur as opposed to phosphorus.  That I can figure out later.  Figure you can attach any R group you want. 

Thanks in advance!!
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Offline critzz

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Re: Name of compound?
« Reply #1 on: January 02, 2015, 07:32:57 PM »
This is a typical Julia-Kocienski reagent, which is used in a modified Julia-olefination (Julia-Kocienski-olefination).
The tetrazole sulfone is generally installed by substituting a hydroxyl group for this sulfide (see below) using the Mitsunobu-reaction, followed by oxidation with H2O2 to obtain the sulfone.


SC1=NN=NN1C2=CC=CC=C2

If I remember correctly, the Julia-Kocienski has indeed a high preference for the (E)-alkene product and is compatible with many functional groups.



Offline discodermolide

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Re: Name of compound?
« Reply #2 on: January 02, 2015, 07:33:29 PM »
This is a Julia olefination (Julia–Kocienski) reaction. For a recent example see DOI: 10.1002/ejoc.201402681
I have a copy of this paper, and others.
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Offline AlphaScent

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Re: Name of compound?
« Reply #3 on: January 02, 2015, 08:09:53 PM »
Thank you guys!!!

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Offline AlphaScent

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Re: Name of compound?
« Reply #4 on: January 02, 2015, 08:22:16 PM »
Thanks Disco.  Just went and got it.

If you're not part of the solution, then you're part of the precipitate

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