ResearchZed
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What is the occurence of meso-configuation in a diamine?
I can't find much information on this (formation of meso's) specifically, and I have two conflicting hypothesis.
On one hand I suspect the formation of a chiral diamine would result in a distribution of chiral centers like such:
2 R,S (meso)
1 S,S
1 R,R
On the other hand I have a suspicion that a meso compound would hardly form at all, potentially due to the first-formed chiral center acting as an
internal chiral auxiliary. Such behavior has been observed in other reactions in which a chiral center forms nearby another chiral center. In this
case, it would mean that the occurrence of meso compounds is unique to each reaction and depends on the structural configuration of the molecule as it
forms.
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Etaoin Shrdlu
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Well, I understood all the words individually. What the devil are you asking about?
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ResearchZed
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Sorry if I was confusing, let me try to rephrase the question.
I am trying to figure out the chiral distribution that would result from aminating p-diacetylbenzene, a pro-chiral diketone. It's
acetophenone with another acetyl group in the para position. The resulting [di]amine has two chiral centers.
Would the resulting distribution be purely racemic, ie 50:50 RR : SS. Or would the distribution be 50:25:25, RS/SR: RR: SS
The reason I am unsure is because I can't find any information on whether or not Meso-compounds are likely to even form, due to the possibility of the
first-formed chiral center acting as an intramolecular chiral auxiliary.
[Edited on 22-1-2016 by ResearchZed]
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Nicodem
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Thread Moved
22-1-2016 at 08:39 |
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