Aryne Compatible Solvents are not Always Innocent

Arynes are important
and versatile intermediates in a variety of
transformations. Commonly used solvents for aryne chemistry include
acetonitrile and dichloromethane. Although rarely reported, the reactive
nature of aryne intermediates makes them prone to side reactions,
which sometimes involve solvent participation. Acetonitrile and dichloromethane
are not always innocent solvents and can participate in aryne-based
reactions. These results are presented in the context of ongoing mechanistic
investigations of the triple aryne–tetrazine reaction.