Metalation of Benzotrifluoride

Aromatic substituents groups which direct ortho-para in electrophilic substitution reactions such as nitration and sulfonation appear to exert a similar influence in the nuclear metalation of substituted benzenes. No studies have been reported of the influence in metalation reactions of groups which lead to meta substitution with electrophilic reagents. In general, reaction of such groups with the customary metalating agents occurs more rapidly than nuclear metalation. In the present work the metalation of benzotrifluoride has been investigated since the trifluoromethyl group is known to be resistant to chemical attack and strongly meta-directing in nitration and in chlorination reactions.