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Demurcuration Radical Mechanism

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bluebunny2020:
Anyone know the mechanism for this process? I've looked all over the internet but haven't found anything on how NaBH4 actually removes Hg-OAc

Thanks ahead of time!

hollytara:
The mechanism I have seen has these steps:

Hydride ion (H-) from borohydride displaces the acetate on mercury to form R-Hg-H

Homolytic cleavage of R-Hg bond.

Transfer of H radical to carbon radical from Hg-H to form R-H bond (C-H) and free mercury metal. 

This was established by Whitesides back in 1970. 

https://pubs.acs.org/doi/pdf/10.1021/ja00725a039 

ch3mist:
Pasto and Gontarz published a similar study on the reduction of -Hg(OAc) with borohydride a year before Whitesides. Same mechanism as the one described above.

JACS 1969, 91(3), 719-721
https://pubs.acs.org/doi/pdf/10.1021/ja01031a036

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