4-acetyl-3,5-diferrocenylcyclohexanone | 1430231-61-0

• 英文名称: 4-acetyl-3,5-diferrocenylcyclohexanone
• CAS: 1430231-61-0
• 化学式: C₂₈H₂₈Fe₂O₂
• 分子量: 508.223
• InChiKey: ZKXWTZMEMGIOAZ-XVJQKJATSA-N

反应信息

• 作为产物：
  描述：

  (E)-(2-ferrocenylvinyl) methyl ketone 在 Dimethylzinc 作用下， 以 甲苯 、 苯 为溶剂， 反应 3.0h， 以45%的产率得到4-acetyl-3,5-diferrocenylcyclohexanone
  参考文献：
  名称：

  Cyclodimerization reactions of the β-ferrocenylvinyl(methyl)ketones in the presence of zinc-organic compounds

  摘要：

  Trans-ferrocenyl-3-buten-2-one 1 undergoes cyclic dimerization with formation of 4-acetyl-3,5-diferrocenylcyclohexanone 5 and 5,8-diferrocenyl-1-hydroxybicyclo-[2.2.2.]octan-3-one 6 in the presence of cyclohexenes and 2-PyZnBr or Me2Zn. No adducts of the Diels Alder reaction of compound 1 in its enolic form with cyclohexenes were observed. Under similar conditions, in the absence of cyclohexenes trans-ferrocenyl-3-buten-2-one 1 affords cyclodimer 5 and cyclotrimer -6-acetyl-4,5,7-triferrocenyl-1,9-dehydro-2-decalone 7,3-(Ferrocenylmethylidene)pentane-2,4-dione 2a and ethyl (E)-2-acetyl-3-ferrocenylacrylate 2b cyclodimerized analogously with formation of 3,5-diferrocenyl-1-hydroxy-2,4,4-triacetylcyclohexene 8a and diethyl 4-acetyl-3,5-diferrocenyl-1-hydroxycyclohexene-2,4-dicarboxylate 8b, respectively. The structures of the obtained compounds were established based on data from IR, H-1 and C-13 NMR spectroscopy, mass spectrometry and X-ray diffraction analysis. The mechanistic aspects of these reactions are discussed. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.02.008