A Combined Experimental and Theoretical Study on the Reaction Mechanism and Molecular Structure of 4-(Diphenylamino)-3-iodo-2(5H)-furanone

作者：Song, Xiumei; Xue, Fuling; Feng, Zongcai; Wang, Yun^*; Wang, Zhaoyang; Xi, Yanli

来源：Australian Journal of Chemistry, 2017, 70(7): 837-844.

DOI：10.1071/CH16616

• 2(5H)-FURANONE DERIVATIVES
• EFFICIENT SYNTHESIS
• BUTENOLIDES
• EXCHANGE

The simultaneous a-iodination and N-beta-arylation mechanism of 5-alkyloxy-4-phenylamino-2(5H)-furanone by (diacetoxyiodo) benzene was investigated by means of density functional theory (DFT) with B3LYP/6-31G/LANL2DZ, selecting 4-(diphenylamino)-5-methyloxy-3-iodo-2(5H)-furanone as the calculation model. In addition, the effect of solvent on the reaction pathway was investigated using the Polarisable Continuum Model (PCM). Good agreement was found between the computational and the experimental results. Furthermore, single crystals of 4-(diphenylamino)-5-ethoxy-3-iodo-2 (5H)-furanone were grown by slow evaporation technique. The molecular structure analysis was performed by single crystal X-ray analysis and theoretical calculations using a semi-empirical quantum chemical method and DFT/B3LYP methods with a LANL2DZ as basis set.

• 出版日期2017