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Polymerization of Alkyl Diazoacetates Initiated with Amidinate/Pd System: Efficient Synthesis of High Molecular Weight Poly(alkoxycarbonylmethylene)s with Moderate Stereoregularity

Abstract

Initiating ability of a new system, amidinate/Pd, for polymerization of diazoacetates is described. The system is effective in affording relatively high number-average molecular weight (Mn) polymers from ethyl diazoacetate (EDA, e.g., Mn = 45,100, 44% yield) and methyl diazoacetate (MDA, e.g., Mn = 26,200, 56% yield) in moderate yield. Polymerization of n-hexyl diazoacetate (nHDA) and benzyl diazoacetate (BDA) by the amidinate/Pd system yields high Mn polymers (Mn = ca. 100,000), although the yield was below 10%. The system is also effective in copolymerization of EDA with nHDA, BDA, and cyclohexyl diazoacetate (cHDA), affording high Mn copolymers in moderate yield. NMR spectra of the products obtained with the system suggest that the polymerization proceeds with significantly higher stereoregularity compared to that with previously reported Pd-based initiating systems.

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Publication details

The article was received on 17 May 2017, accepted on 17 Jun 2017 and first published on 19 Jun 2017


Article type: Paper
DOI: 10.1039/C7PY00816C
Citation: Polym. Chem., 2017, Accepted Manuscript
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    Polymerization of Alkyl Diazoacetates Initiated with Amidinate/Pd System: Efficient Synthesis of High Molecular Weight Poly(alkoxycarbonylmethylene)s with Moderate Stereoregularity

    H. Shimomoto, J. Kawamata, H. Murakami, K. Yamashita, T. Itoh and E. Ihara, Polym. Chem., 2017, Accepted Manuscript , DOI: 10.1039/C7PY00816C

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