Sciencemadness Discussion Board

Radical Attack of NaCN?

KingBoo - 23-8-2013 at 10:24

I saw a journal of a tertiary halogenated carbon reacting with NaCN in DMSO under UV.

So I know that it was a radical attack, but how would a radical attack an anion?

Also, the journal reported a very high yield for this reaction(73%). I had the understanding that radical reactions are very messy. Why doesn't the radical pluck a hydrogen from DMSO?

Lastly, could a radical attack CO2 to form a carboxy group on the tertiary carbon? Or would it attack the Oxygen's instead?

Thanks :)

Polverone - 23-8-2013 at 12:38

Please provide a citation for the reaction you read about. Threads opened without references are not appropriate for Organic Chemistry.

KingBoo - 23-8-2013 at 12:58

http://www.ncbi.nlm.nih.gov/pubmed/15151394

Sorry about that, thought it would be universal.