Synthesis of 1,1'-Ferrocenediyl Salicylaldimine Ligands and Their Application in Titanium-Initiated Lactide Polymerization

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• 作者：Robert C. J. Atkinson ; Kathryn Gerry ; Vernon C. Gibson ; Nicholas J. Long ; Edward L. Marshall ; Lara J. West
• 刊名：Organometallics
• 出版年：2007
• 出版时间：January 15, 2007
• 年：2007
• 卷：26
• 期：2
• 页码：316 - 320
• 全文大小：86K
• 年卷期：v.26,no.2(January 15, 2007)
• ISSN：1520-6041

文摘

The synthesis of bidentate N/O 1,1'-ferrocenediyl analogues of N-aryl-salicylaldimines has beenaccomplished from the previously unreported 1'-hydroxyferrocenecarbaldehyde, 3. Thus, the reaction of3 with 2,6-diisopropylaniline and with aniline leads to the isolation of N-(2,6-diisopropylphenyl)-(1'-(hydroxy)ferrocenyl)aldimine, 5, and N-phenyl-(1'-(hydroxy)ferrocenyl)aldimine, 6, respectively. However,attempts to synthesize analogues of bis(iminophenoxide) (salen) ligands by treatment of 3 with 1,2-ethylenediamine and with trans-(+/-)-1,2-diaminocyclohexane led to intractable product mixtures, whilereaction with 1,2-phenylenediamine resulted in formation of a substituted benzimidazole. Titanium bis(isopropoxide) complexes of 5, 6, and, for comparative purposes, 1'-(diphenylphosphino)hydroxyferrocenehave been synthesized, and in a preliminary study all three complexes were found to initiate the ring-opening polymerization of rac-lactide in a well-controlled manner.