Sciencemadness Discussion Board

What solvent can be used for free radical reactions

Triflic Acid - 16-4-2021 at 05:25

I'm going to try the hunsdiecker reaction soon, but its supposed to be carried out in c-tet :( I saw that MeCN works, but won't this cause side reactions when the radicals interact with the hydrogens on the Me? Also, I'm thinking of using a aromatic polar solvent, since those shouldn't react with radicals. Would something like furan work, since its polar and can dissolve both the iodine and the silver salt?

HeYBrO - 16-4-2021 at 21:17

MeCN tends to work very well for radical reactions in my experience- but it is all about the BDE; MeCN BDE for C-H is ca. 389 kj/mol and C-Cl in CCl4 is 293 kj/mol (both at 298 K) so it should work. Maybe try on a small scale first? I wouldn't use furan