Metalation of olefinic positions in norbornadiene: enhancement and attenuation of kinetic CH-acidities by a neighboring enesilane moiety
When treated with BuLi in the presence of Na or K tert-butoxide, 2-(trimethylsilyl)- and 2-(triethylsilyl)norbornadiene undergo H/metal-exchange mainly at the 5-position. The latter position is slightly activated relative to unsubstituted norbornadiene while the 2 other olefinic positions prove to be a quite inert. Two side reactions are obsd.: the metalation of Si-attached Me groups and the replacement of the entire trialkylsilyl group by a metal atom. [on SciFinder (R)]
Keywords: Lithiation (of trialkylnorbornadienes ; by butyllithium in presence of alkali metal tert-butoxide) ; lithiation trialkylsilylnorbornadiene; norbornadiene trialkylsilyl lithiation; silylnorbornadiene trialkyl lithiation
Organometallic and Organometalloidal Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
written in English.
16205-92-8 (2-Trimethylsilylnorbornadiene); 107905-60-2 Role: RCT (Reactant), RACT (Reactant or reagent) (lithiation of, by butyllithium in presence of alkali metal tert-butoxide)
Record created on 2006-03-03, modified on 2016-08-08