The Vespiary
The Hive => Chemistry Discourse => Topic started by: amalgum on September 30, 2001, 08:34:00 PM
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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?
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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.
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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.
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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
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:-[ Whoops, quite correct.
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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.