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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: kamiyu on May 13, 2014, 06:58:22 AM

Title: About 1,4-diiodobutane
Post by: kamiyu on May 13, 2014, 06:58:22 AM

Hi
Recently I used a reagent called 1,4-diiodobutane. The label says it is stabilized by trace amount of Cu.
Does anyone know the stabilizing effect of copper in this context?
Thanks

Title: Re: About 1,4-diiodobutane
Post by: clarkstill on May 13, 2014, 01:07:00 PM

It's a good question! Copper is often present as an additive in commercial alkyl halides, and is often also added when distilling such compounds.  It clearly stabilizes the compounds (if you do the distillation without it it turns black and horrible), but no one has ever explained to me mechanistically how it does this!  If anyone knows the answer, please share!

Title: Re: About 1,4-diiodobutane
Post by: clarkstill on May 20, 2014, 01:15:47 PM

Nobody?

Title: Re: About 1,4-diiodobutane
Post by: Babcock_Hall on May 20, 2014, 02:37:47 PM

I will be working with this reagent soon.  I used to work with TMSI also, I think that this compound is sometimes stored over copper shot.  I assumed that the copper acts as a one-electron reducing agent, which somehow prevents oxidation of the reagent to iodine (I₂) and something else.  But I have never researched it.