amalgum (Stranger)
09-30-01 20:34
No 218928
      cis and trans  Bookmark   

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?
(Old P2P Cook)
09-30-01 21:43
No 218943
      Re: cis and trans  Bookmark   

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.
09-30-01 22:15
No 218954
      Re: cis and trans  Bookmark   

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.
(Distinctive Doe)
09-30-01 23:17
No 218964
      Re: cis and trans  Bookmark   


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
(Old P2P Cook)
10-01-01 00:53
No 218981
      Re: cis and trans  Bookmark   

blushWhoops, quite correct.
10-01-01 12:09
No 219100
      Re: cis and trans  Bookmark   


   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.