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Topic: (R)-3,3'-dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl synthesis  (Read 1883 times)

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Offline Ena_pjena

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(R)-3,3'-dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl synthesis
« on: September 05, 2016, 10:26:42 AM »
I need a help with understanding this mechanisam. Why do we need to dissolve Compound 2 in the Et2O, what is happing and why do we add nBuli and then stirred the mixture for 3 h? Why do we add THF separately and then stirred for 1 h? Why do we add 1,2-dibrimotetrachloroethane ? And what about eq?

Thanks in advance!

P.S. see attachment
 
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Offline kriggy

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Re: (R)-3,3'-dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl synthesis
« Reply #1 on: September 05, 2016, 10:45:57 AM »
What do you think?
How BuLi reacts?
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Offline rolnor

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Re: (R)-3,3'-dibromo-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl synthesis
« Reply #2 on: September 06, 2016, 10:57:38 AM »
I think diethylether has weaker interaction with BuLi, letting the methoxymethylgroups directing BuLi to the ortho position. For me less clear why THF is added later, maby the lithiated compound becomes more reactiv in prescence of THF?
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