Gorecka, JoannaHeiss, ChristopheScopelliti, RosarioSchlosser, Manfred2006-03-032006-03-032006-03-03200410.1021/ol0480022https://infoscience.epfl.ch/handle/20.500.14299/227014WOS:0002252802000505884(2,6-Dichlorophenyl)- and (2,6-dibromophenyl)trialkylsilanes undergo hydrogen/metal interconversion preferentially at the 4- rather than 3-position. However, the organometallic species generated by such a \"meta metalation\" are thermodynamically less stable (i.e., more basic) than those that would result from an ordinary \"ortho metalation\". This was demonstrated by equilibration expts. based on permutational halogen/metal interconversion. A new buttressing effect can explain the unprecedented regioselectivity. It is supported by X-ray structures that reveal marked deformations of the benzene ring in halophenylsilanes. [on SciFinder (R)]Deprotonation; Steric effects (buttressing effects on haloarene deprotonation kinetics or thermodn. phenomenon); Aromatic hydrocarbons Role: CPS (Chemical process)FMU (Formationunclassified)PEP (Physicalengineering or chemical process)PRP (Probuttressing effect haloarene deprotonation kinetic thermodn phenomenontext::journal::journal article::research article