Massive electrostatic effects on heteropolar C-C disconnections: Transforming a phenyl anion into a potent leaving group

Abstract

The SASAPOS protocol - a general reaction sequence which allows the complete exchange of various neutral ligands X in organic, elementorganic, and inorganic systems by cationic ligands L+ - has been applied to a small variety of pentafluoro benzene derivatives C6F5-E (E = -C(O)H, -C(N-Ph) H, -PCl2/-P(L+)2, -H) yielding the ion clusters C6(L+)5-E (F 3CSO3-)5. The reaction conditions required to observe a heteropolar C-C or C-P disconnection, with a highly stabilized pentakisonio-substituted phenyl anion as the key intermediate, are specified. When E = H, the latter compound also figures as the key intermediate during H/D exchange under basic conditions. © Wiley-VCH Verlag GmbH & Co. KGaA, 2005.