Citation: LI Xu-Dong, WANG Hui, LI Jun-Qiu, MEN Yi-Can, QU Hong-Mei. Zirconium-mediated Synthesis and Crystal Structure of 3,6-Diiodo-4,5- dialkyl-phthalic Acid Dimethyl Ester[J]. Chinese Journal of Structural Chemistry, ;2015, 34(9): 1347-1356. doi: 10.14102/j.cnki.0254-5861.2011-0686 shu

Zirconium-mediated Synthesis and Crystal Structure of 3,6-Diiodo-4,5- dialkyl-phthalic Acid Dimethyl Ester

1.
Key Laboratory of Systems Bioengineering, Ministry of Education, Tianjin Key Laboratory of Biological and Pharmaceutical Engineering, Department of Pharmaceutical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China

Corresponding author: QU Hong-Mei,
Received Date: 14 February 2015
Available Online: 6 May 2015

A novel series of para-diiodobenzene derivatives, 3,6-diiodo-4,5-dialkyl-phthalic acid dimethyl esters, were prepared via cycloaddition of two TMS-substituted alkynes and dimethyl acetylenedicarboxylate, which was mediated by zirconocene. After iodination, three new compounds of 3,6-diiodo-4,5-dimethyl(dipropyl, dibutyl)-phthalic acid dimethyl esters (3a, 3b, 3c) were synthesized in high region-selectivity and yields, and characterized by NMR. The crystal structures were determined by single-crystal X-ray diffraction. The crystal of 3a (C₁₂H₁₂I₂O₄, M_r=474.02) belongs to the triclinic system, space group P1 with a=7.6238(10), b=9.4571(12), c=10.8221(14) Å, α=66.611(10), β=88.511(12), γ=77.604(11)°, V=697.93(16) Å³, Z=2, F(000)=444, D_c=2.256 mg/m³, µ=4.509 mm⁻¹, T=133(2) K, S=1.014, R=0.0229 and wR=0.0547 for 2644 observed reflections with I>2σ(I); the crystal of 3b (C₁₆H₂₀I₂O₄, M_r=530.12) is of triclinic system, space group P1 with a=9.4122(19), b=10.626(2), c=11.353(2) Å, α=97.90(3), β=113.83(3), γ=110.22(3)°, V=922.6(3) Å³, Z=2, F(000)=508, D_c=1.908 mg/m³, µ=3.422 mm⁻¹ , T=113(2) K, S=1.115, R=0.0428 and wR=0.1072 for 3971 observed reflections with I>2σ(I); the crystal of 3c (C₁₈H₂₄I₂O₄, M_r=558.17) belongs to the monoclinic system, space group P2₁/c with a=26.396(2), b=8.7560(8), c=25.7970(18) Å, β=91.721(4)°, V=5959.6(8) Å³, Z=12, F(000)=3240, D_c=1.866 mg/m³, µ=3.184 mm⁻¹, T=113(2) K, S=1.154, R=0.0424 and wR=0.0766 for 13056 observed reflections with I>2σ(I).
- zirconocene,
- 3,6-diiodo-4,5-dialkyl-phthalic acid dimethyl ester,
- para-diiodobenzene derivative,
- crystal structure,
- X-ray diffraction,
- NMR
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