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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)]

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