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Synthesis of lithium and aluminum complexes supported by [OC(But)CHP(Ph2)=NBut]− ligand and catalysis of [R2Al{OC(But)-CHP(Ph2)=NBut}] (R = Me, Et) and [Me2Al{1-{OC(Ph)CH}-3-R1-5-MeC3HN2}] (R1 = Me, But) in the ring-opening polymerization of ɛ-caprolactone

  • Article
  • Organic Chemistry
  • Published:
Chinese Science Bulletin

Abstract

A series of lithium and aluminum complexes bearing [OC(But)CHP(Ph2)=NBut]− ligand were synthesized and characterized. Reaction of ButC(O)CH2Br with Ph2PNHBut afforded [Ph2P(NHBut)CH2C(O)But]+Br− (1). Treatment of 1 with excess of NaH in THF generated ligand precursor Ph2P(CH2C(O)But)=NBut (2). Reaction of 2 with AlR3 (R = Me, Et) gave N,O-chelate aluminum complexes [R2Al{OC(But)CHP(Ph2)=NBut}] (3, R = Me; 4, R = Et). Lithiation of 2 with an equiv. of LiBun formed lithium complex [Li{OC(But)CHP(Ph2)=NBut}] (5). Reaction of the lithium complex with an equiv. of AlCl3 yielded [Cl2Al{OC(But) CHP(Ph2)=NBut}] (6). Complex 6 was also obtained by reaction of 3 with an equiv. of AlCl3. Compounds 2–6 were characterized by NMR spectroscopy, elemental analysis and single crystal X-ray diffraction techniques (for 2, 3 and 6). Catalysis of complexes 3 and 4 as well as [Me2Al{1-{OC(Ph)CH}-3-R1-5-MeC3HN2}] (R1 = Me, But) toward the ring-opening polymerization of ɛ-caprolactone was investigated.

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Authors and Affiliations

  1. Department of Chemistry, University of Science and Technology of China, Hefei, 230026, China

    Die Yang, CuiFang Cai & ZhongXia Wang

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  1. Die Yang
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  2. CuiFang Cai
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Correspondence to ZhongXia Wang.

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Yang, D., Cai, C. & Wang, Z. Synthesis of lithium and aluminum complexes supported by [OC(But)CHP(Ph2)=NBut]− ligand and catalysis of [R2Al{OC(But)-CHP(Ph2)=NBut}] (R = Me, Et) and [Me2Al{1-{OC(Ph)CH}-3-R1-5-MeC3HN2}] (R1 = Me, But) in the ring-opening polymerization of ɛ-caprolactone. Chin. Sci. Bull. 55, 2896–2903 (2010). https://doi.org/10.1007/s11434-010-3167-7

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  • DOI: https://doi.org/10.1007/s11434-010-3167-7

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