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Topic: How to suppress the product through the 1,3-dipolar mechanism?  (Read 5246 times)

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Offline zhubo

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How to suppress the product through the 1,3-dipolar mechanism?
« on: September 28, 2006, 12:04:15 AM »
Recently, I found a reaction, but there were two products. I guess there may be two mechanisms, one radical mechanism, the other 1,3-dipolar mechanism. I wonder how to suppress the product through the 1,3-dipolar mechanism. Any input is appreciated.

Offline bontempo

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Re: How to suppress the product through the 1,3-dipolar mechanism?
« Reply #1 on: September 29, 2006, 05:42:06 AM »
Could you give just a little bit more information? We won't steal your reaction...  ;D

From what you've said, it seems that you should try and shut down mechanistic pathways involving charged/polarised species. One of the easiest ways to (try) to do so is a change of solvent. Try something less polar with a lower dieletric constant. But since we don't know which solvent you're actually using..
Also, you might want to repeat the reaction adding some ditert-butylphenol as a radical trap. If you obtain only (or mainly) the dipolar cycloaddition product, that gives some assurance as to the radical nature of the process leading to your "new" product.

Offline zhubo

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Re: How to suppress the product through the 1,3-dipolar mechanism?
« Reply #2 on: September 29, 2006, 11:56:53 AM »
bontempo, thank you!
Chlorobenzene was the solvent used in my reaction. Could you give some more suggestion about the solvent which should be used in the reaction?

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