Acidity enhancement through homoconjugation: selective introduction of sodium into olefinic positions
When treated with BuLi and Me3CONa, both norbornadiene and norbornene underwent a H/Na-exchange at the 2-position. The diene, however, reacted approx. 30 times faster with Me3SiCl. Bicyclo[3.2.0]hepta-2,6-diene was also more readily metalated than bicyclo[3.2.0]hept-6-ene and its 7-position was preferentially attacked. Under the same conditions, cycloheptatriene was silylated at the 2-position only. [on SciFinder (R)]
Keywords: Metalation (of bicycloheptenes ; -adienes ; and cycloheptatriene ; with butyllithium and sodium tert-butoxide ; selectivity of); Silylation (of metalated bicycloheptenes ; -adienes ; and cycloheptatriene); Regiochemistry (of metalation in bicycloheptenes ; -ad ; acidity enhancement homoconjugation norbornadiene; metalation selectivity cycloheptatriene; silylation selectivity cycloheptatriene; silylation selectivity cycloheptatriene
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
written in English.
121-46-0; 498-66-8; 544-25-2; 2422-86-8; 4927-03-1 Role: RCT (Reactant), RACT (Reactant or reagent) (metalation and silylation of); 2422-86-8 Role: RCT (Reactant), RACT (Reactant or reagent) (metalation and silylations of); 16205-87-1P; 16205-92-8P; 67403-68-3P; 101536-83-8P; 101536-84-9P; 101536-85-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Record created on 2006-03-03, modified on 2016-08-08