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The synthesis of 4‐(3,3,3‐trifluoro‐2‐trifluoromethyl‐1‐propenyl)‐1,3‐thiazole derivatives from 5,5,5‐trifluoro‐4‐(trifluoromethy)‐3‐penten‐2‐one is described. Attention is mainly focused on 2‐N‐phenylamino‐4‐(3,3,3‐trifluoro‐2‐trifluoromethyl‐1‐propenyl)‐1,3‐thiazole. Structural and conformational studies using several spectroscopic methods (FT‐IR, NMR, Raman, x‐ray, MS) were performed. Geometry optimization and prediction of vibrational and magnetic properties were carried out using ab initio Hartree–Fock (HF) and density functional theory (DFT) calculations to assist the spectroscopic analysis. Copyright © 2004 John Wiley & Sons, Ltd.

The experimental 1H and 13C NMR spectra of 13 phenyl cinnamates and four 4‐methylcoumarins were investigated and their chemical shifts assigned on the basis of the two‐dimensional spectra. For the unsubstituted cinnamic acid phenyl ester, optimized molecular structures were calculated at a B3LYP/6‐311++G(d,p) level of theory. 1H and 13C NMR chemical shifts were also calculated with the GIAO method at the B3LYP/6‐311 + G(2d,p) level of theory. The comparison between experimental and calculated NMR chemical shift suggests that the experimental spectra are formed from the superposition spectra of the two lowest energy conformers of the compound in solution. The most stable s‐cis configuration found in our studies is also the conformation adopted for a related phenyl cinnamate in solid state. The experimental results were analyzed in terms of the substituent effects. Copyright © 2013 John Wiley & Sons, Ltd.

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