リチウムイオンによって加速されたクアドリシクランからノルボルナジエンへの原子価異性化反応

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タイトル別名
  • Valence-isomerization Reaction of Quadricyclane to Norbornadiene Promoted by Lithium TFPB
  • リチウム イオン ニ ヨッテ カソク サレタ クアドリシクラン カラ ノルボルナジエン エ ノ ゲンシカ イセイカ ハンノウ

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抄録

Thermally-forbidden reactions of quadricyclane to norbornadiene were accelerated by a catalytic amount of alkaline salts, where the presence of water and the nature of the counter anion and solvent affected the rate. Non-hydrated, highly electrophilic lithium ions obtained from Lithium tetrakis(3,5-bis(trifluoromethyl)phenyl)borate (LiTFPB) promotes the valence-isomerization of quadricyclane to norbomadiene extremely; the relative rates in the presence of LiTFPB, LiTFPB・H_2O, and NaTFPB are 470:76:2.7 in CDCl_3 and 297:9.7:1 in C_6D_5CD_3. This is explained by the difference of the binding energy of lithium and sodium ion. The rates in CDCl_3 are higher than those in C_6D_5CD_3, which is supported by theoretical calculations.

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