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cis and trans

Started by amalgum, September 30, 2001, 08:34:00 PM

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amalgum

What is the difference between the cis and trans isomers of safrole other than them being structured different.  Is one more potent than the other?

terbium

The better question might be - what is the difference in reactivity of the safrole cis and trans isomers during a Wacker oxidation. To which the answer would probably be - not much.

Cis and trans safrole both convert into exactly the same ketone. So once you have the ketone the difference is gone.

amalgum

Actually I wasnt worried about reactivity.  I was just wondering if use of a different isomer would yeild a better product in the long run.  But since you brought it to my attention that it goes to the same ketone, I guess all I can say is nevermind.

foxy2

Terbium

I think  I saw a reference that said the reactivity of the cis was somewhere around 9 times faster than the trans.   If I remember right it was for an epoxidation reation. Don't quote me on this because my memory is foggy and I have no idea where I read it.
:)

Do Your Part To Win The War

terbium


riobard

Foxy,

   I think you're right about the rate being 9X faster for cis-isosafrole than trans-isosafrole. The cis- isomer is a bit less hindered for the peracid to approach the isosafrole molecule's double bond, so it should react more quickly. Epoxidations only goe through a single step, so no wierd chemistry in involved as far as I can see.