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二茂铁基长链烷基β-二酮的合成及表征
Synthesis and Characterization of Ferrocenyl Long-Chain Alkyl β-Diketones
【摘要】 通过乙酰基二茂铁与酯的缩合反应,合成了五个二茂铁基长链烷基β─二酮化合物FcCOCH_2COC_nH_(2n+1)(Fc=C_5H_5FeC_5H_4,n=5~9)。用元素分析、UV─Vis、IR、1 ̄HNMR、MS对化合物进行了表征。测试结果表明,β─二酮化合物仅以烯醇形式存在。
【Abstract】 he five new Ferrocenyl long-chain alkyl β-diketones with a general formulaC5H5FeC5H4COCH2COCnH2n+1 (n=5-9) were synthesized by Claisen condensation of acetylferro-cene with ester. These compounds were characterized by elementary analysis, UV-Vis,IR, 1 ̄HNMR and MS spectra. The β-diketones show a sawtoothed increase in melting point withincreasing carbon number of alkyl group. There are three absorption bands at about 268nm,310nm and 452nm in the UV-Vis spectra. The absorption band observed at 310nm is due to the π-π ̄* transition of intramolecular hydrogen bonded chelate ring. The IR spectra show the character-istic absorptions of η ̄5-Cp group at about 3104cm ̄(-1), 1112cm ̄(-1), 1004cm ̄(-1) and 824cm ̄(-1), and νOH,ν(O-C)、ν(C-O) for the enol form near 3432cm ̄(-1)、1619cm ̄(-1) and 1554cm ̄(-1). In 1 ̄HNMR spectra, the pres-ence of OH protonic chemical shifts in the 15.90~15.70×10 ̄(-6) region also indicate that the exis-tent state of the β-diketones is in the enol form. The molecular ion peak at m/e 354 (relative in-tensity 86%), and peaks of major cationic fragments C5H5FeC5H4C≡O ̄+ (m/e213, 28%),[C5H5FeC5H4] ̄+ (m/e185, 57%) and + ̄O≡CCH2COC7H15 (m/e169, 36%) in the FAB-mass spec-trum of compound Ⅲ was observed.
- 【文献出处】 内蒙古大学学报(自然科学版) ,ACTA SCIENTIARUM NATURALIUM UNIVERSITATIS NEIMONGOL , 编辑部邮箱 ,1994年05期
- 【分类号】O623.523
- 【被引频次】12
- 【下载频次】110