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Radicals in organic chemistry Propose a mechanism

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ChemGeek

(@chemgeek)

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Topic starter 01/12/2021 9:25 am

Hi)

I know that this reaction proceeds via a radical mechanism. But I cannot really propose a detailed mechanism 😥

What do you think about it?

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mechanism radical exercise

Amalgama

(@amalgama)

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Posts: 344

01/12/2021 10:00 pm

Why do you think this is a radical reaction?

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ChemGeek

(@chemgeek)

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Topic starter 04/12/2021 11:25 am

@amalgama The professor mentioned it during a lecture

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FreeSoul

(@igorgordiy)

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Posts: 70

08/12/2021 7:16 am

@chemgeek

Hey there!

I have searched a bit this reaction and found the following mechanism: First the diradical formation occurs. The halide ion then donates its two electrons in the formation of a new Br-C bond and radical electron involved is believed to shuttle over a transient C1-C4 bond forming the anion intermediate B. The anion is a powerful base, stripping protons even from DMSO to final product.

See the original paper link for more details: https://pubs.acs.org/doi/10.1021/ja070023e

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