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Boron Trifluoride Etherate
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Topic: Boron Trifluoride Etherate (Read 2151 times)
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AlphaScent
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Boron Trifluoride Etherate
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January 03, 2015, 10:03:04 PM »
Does anyone have a good reference about this reagent and how it helps with epoxide opening?
A good read about the nature of the compound, if you will?
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discodermolide
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Re: Boron Trifluoride Etherate
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January 04, 2015, 12:27:23 AM »
It coordinates to the oxygen atom hence causing the carbons to be prone to nucleophillic attack.
The reagent is very corrosive. Fumes in moist air, and is flammable. Not a particularly nice compound
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AlphaScent
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Re: Boron Trifluoride Etherate
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January 04, 2015, 02:01:07 PM »
Thanks Disco!!
I understand that it is a commonly used Lewis acid. I was just looking for a good read about when it should be used and all that. From what you said it seems you really do not want to and should find another Lewis acid when possible.
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discodermolide
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Re: Boron Trifluoride Etherate
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January 04, 2015, 02:26:39 PM »
It is a great LA when you are dealing with oxygen containing systems, like epoxides, enolates and the like. It can be easily handled on scale. Buffered work ups to avoid it becoming too acidic. Avoid reducing conditions.
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