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)]


Published in:
Chimia, 39, 7-8, 229-30
Year:
1985
Keywords:
Note:
CAN 104:206757
24-7
Alicyclic Compounds
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0009-4293
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)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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