N-phenyl-1-ferrocenylbicyclo[5.4.0]undec-10(11)ene-2,3-dicarboximide | 288627-03-2

• 英文名称: N-phenyl-1-ferrocenylbicyclo[5.4.0]undec-10(11)ene-2,3-dicarboximide
• CAS: 288627-03-2
• 化学式: C₂₉H₂₉FeNO₂
• 分子量: 479.402
• InChiKey: NWWGRVDIUFYILJ-GIKGXCNBSA-N

反应信息

• 作为反应物：
  描述：

  N-phenyl-1-ferrocenylbicyclo[5.4.0]undec-10(11)ene-2,3-dicarboximide 在 air 作用下， 以58%的产率得到N-phenyl-1-ferrocenyl-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,3-dicarboximide
  参考文献：
  名称：

  The behavior of 3-ferrocenyl-1-methyl-1,2-pentamethyleneallyl and 1,5-diferrocenyl-3-methyl-2,4-tetramethylene-1,4-dienyl carbocations in the cationic dimerization of 1,3-dienes

  摘要：

  3-Ferrocenyl-1-methyl-1,2-pentamethyleneallyl carbocation 9 and 1,5-diferrocenyl-3-methyl-2,4-tetramethylene-1,4-dienyl carbocation 10 are transformed into linear 21 and cyclic 28 dimers, respectively, in low yields under conditions of the cationic dimerization (treatment with N,N-dimethylaniline). The former is preferentially deprotonated into 1-ferrocenylmethylidene-2-methylidenecycloheptane (19) and 3-ferrocenylmethylidene-2-methylcycloheptene (20), while the latter is reduced into 1,3-bisferrocenylmethylidene-2-methylcycloheptane (26). However, a linear dimer was obtained in the reaction of salt 9 with s-cis-diene 19, while the reaction of salt 10 with 1,3-bisferrocenylmethylidene-2-methylidenecycloheptane (27) results in a cyclodimer 28 together with a linear dimer 29. The results obtained corroborate the stepwise mechanism of cationic cycloaddition of 1,3-dienes and manifest the role of the electronic factor in the intramolecular cyclization of an intermediate linear dimeric allylic cation. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(00)00135-2