AIBN: Azobisisobutironitrile
ABCN or ACHN: Azobis(cyclohexanecarbonitrile)
Ref: Inorg Chem 2003 42, 2908-2918 for the usual bromination reaction of 4'-(p-Tolyl)-2,2':6',2''-terpyridine with N-Bromosuccinimide (NBS) in CCl4 with AIBN.
Motivation: in my country, Sigma only sells solutions (acetone or toluene) of AIBN, which I am not used to.
As sigma sells ACHN (or ABCN) in a solid form and claims it is a better radical initiator than AIBN, I would like to try this but I am worried it could completely fail due to simple solubility considerations of ACHN in CCl4.
Many thanks for any help.
Sigma says ABCN is soluble in a variety of solvents. Looking at the structure, I do not see why it should be less soluble in CCl4 than AIBN. So it is worth a try. But you need to take care of the half-life of this compound. Wikipedia and other sources say it is 10 h at 88 °C. This is much longer than the half-life of AIBN (1 h at about the same temperature). The boiling point of CCl4 is 77 °C. The overall time for this Wohl-Ziegler reaction to reach completion may be significantly longer than with AIBN (although this is a radical chain reaction). Using more initiator could be a solution in case of problems.
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