3-ferrocenylmethylidene-2-methylcycloheptene | 288406-01-9

• 英文名称: 3-ferrocenylmethylidene-2-methylcycloheptene
• CAS: 288406-01-9
• 化学式: C₁₉H₂₂Fe
• 分子量: 306.231
• InChiKey: OOQMIFDCZNJQRM-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  tetrafluoroboric acid 、 3-ferrocenylmethylidene-2-methylcycloheptene 以>99的产率得到E-1-ferrocenylmethylidene-2-methylcycloheptan-2-yl tetrafluoroborate
  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