A degassed mixture containing 0.245 mmol cyclohexene and 0.05 mmol N-hydroxyphthalimide (NHPI),1,2 in 5 mL acetonitrile was added to a degassed solution of lead tetraacetate3 (0.025 mmol in 5 mL acetonitrile) under nitrogen atmosphere at room temperature. After the completion of the reaction, the solvent and the olefin excess was removed under reduced pressure and the residue was purified by preparative TLC using hexane:ethyl acetate = 2:1 as eluent, giving the above product.
1H-NMR (400 MHz, CDCl3): d= 7.86, 7.77 (Ar, 4 H); 6.10, 5.97 (CH=CH, 2H); 4.77 (O-CH, 1H); 2.17, 2.04, 2.01, 1.85 (CH2, 8H).
13C-NMR (100 MHz, CDCl3): d= 164.7 (C=O); 134.8, 124.3 (Ar); 81.3 (C-O); 77.4 (C=C); 27.7, 24.6, 21.3 (CH2).
Supplementary Materials
Supplementary File 1Supplementary File 2Supplementary File 3References
- Ishii, Y.; Sakaguchi, S.; Iwahama, T. Adv. Synth. Catal. 2001, 343, 393. [CrossRef]
- Masui, M.; Hosomi, K.; Tsuchida, K.; Ozaki, S. Chem. Pharm. Bull. 1985, 33, 4798.
- Martin, J.C.; Taylor, J.W.; Drew, E.H. JACS 1967, 89, 129.
- Sample Availability: Available from MDPI.
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