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Topic: Favorskii reaction  (Read 8207 times)

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Offline HP

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Favorskii reaction
« on: February 20, 2006, 03:34:44 PM »
Do this new topic as a continuation of the writen in topic "CH3COCH3 to CH3COOH". The first question is what the difference betw Favorskii reaction and the Favorskii rearangement? Please dont lough many to my particular ignorance friends  :P
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Offline Albert

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Re:Favorskii reaction
« Reply #1 on: February 20, 2006, 03:36:24 PM »
This is the part of the synthesis of cortisone where a Favorskii reaction (or rearrangement) is carried out.

It's not extremely detailed, but I think it's sufficiently clear.
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Offline HP

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Re:Favorskii reaction
« Reply #2 on: February 20, 2006, 03:46:26 PM »
Nice scheme Albert! Now clear for me how forming the unsaturated acid moestry. Do you know how synthesized the starting compound? I think not from bromination COCH3 moestry but may be by some kind functualization with dibromoacetic acid  ???
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Offline Mitch

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Re:Favorskii reaction
« Reply #3 on: February 20, 2006, 03:52:04 PM »
Don't we have this in our name reactions section?
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Offline Albert

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Re:Favorskii reaction
« Reply #4 on: February 20, 2006, 04:03:16 PM »
here we are
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Offline HP

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Re:Favorskii reaction
« Reply #5 on: February 20, 2006, 04:10:36 PM »
Yes Mitch theres Favorskii rearangement described in Name Reactions. My question is if this reaction mechanism is the same when using only NaOH as base or theres some difference when using Na-alcoholat base. I think theres no cyclization stage in reaction CH3COCH2Br with NaOH and then we have CH3HOC(O:-)CH2+ formation and then CH3 "jump" to form propionic acid.
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Offline HP

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Re:Favorskii reaction
« Reply #6 on: February 20, 2006, 04:15:36 PM »
Fine synthesis Albert. Now i remember i have seen something similar reaction with diethyloxalate...What do you think about possible Br2 addition to the double bond in the first ring?
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Offline Albert

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Re:Favorskii reaction
« Reply #7 on: February 20, 2006, 04:24:41 PM »
I daresay that the COCOOEt motif gives the reaction a certain specificity.
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Offline HP

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Re:Favorskii reaction
« Reply #8 on: February 20, 2006, 04:31:08 PM »
Really fine and exquisite synthesis! Specificity art in chemistry :) Goodnight from me hope in dreams i'll foresee something ;)
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