Heiss, ChristopheRausis, ThierrySchlosser, Manfred2006-03-032006-03-032006-03-03200510.1055/s-2005-861787https://infoscience.epfl.ch/handle/20.500.14299/227040WOS:0002277748000206611Deprotonation-triggered heavy halogen migrations should become a favorite tool in arene synthesis if their occurrence and outcome could be made predictable. Particularly attractive, though extremely rare, are stop-and-go situations where a first intermediate, generated by metalation, can be trapped at -100 DegC, whereas at -75 DegC halogen migration gives rise to an isomer. As shown now, one can conveniently produce the initial aryllithium species by halogen/metal interconversion in toluene at -100 DegC, under conditions that preclude halogen migration, and unleash the isomerization process by adding THF at -75 DegC. [on SciFinder (R)]Basicity; Isomerization; Solvent effect (haloaryllithium isomerizations in arene synthesis based on differential basicities and solvent effects); Rearrangement (halogen; haloaryllithium isomerizations in arene synthesis based on differential basicitieshaloaryllithium isomerization basicity solvent effect; aryl carboxylic acid prepntext::journal::journal article::research article