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Topic: Why is it possible to transmetallate i-PrMgBr with PhBr but not the other way?  (Read 1945 times)

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Offline Vrig

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Why is it possible to transmetallate i-PrMgBr with PhBr but not the other way?
« on: January 22, 2013, 11:41:45 AM »
Q: Why is it possible to transmetallate i-PrMgBr with PhBr to generate i-PrBr and PhMgBr, but not the other way around?

I suspect that it has something to do with the hybridization of i-Pr vs Ph (Ph would have a more stable anion, which pKa also shows) but I don't understand how it would effect the mechanism unless the intermediate is a phenylic anion?
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