Sergiu Coseri

Institute of Macromolecular Chemistry “P.Poni” Iasi, Gr.Ghica Voda, 41A, 6600 Iasi, Romania and

National Research Council of Canada, 100 Sussex Dr., Ottawa, ON, K1A 0R6, Canada

e-mail: [email protected]

Received: 30 September 2005 / Accepted: 24 October 2005 / Published: 22 January 2006

A degassed mixture containing 0.38 mmol cyclooctene and 0.0767 mmol N-hydroxyphthalimide (NHPI),^1,2 in 5 mL acetonitrile was added to a degassed solution of lead tetraacetate³ (0.038 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=7.84, 7.77 (Ar, 4 H); 5.86, 5.77 (CH=CH, 2H); 5.32 (O-CH, 1H); 2.22, 2.10, 1.67, 1.61, 1.59 (CH₂, 10H).

¹³C-NMR (100 MHz, CDCl₃): d= 164.6 (C=O); 134.9, 128.2 (Ar); 85.7 (C-O); 77.6 (C=C); 33.7, 30.5, 28.7, 26.7, 24.6 (CH₂).

References

1. Ishii, Y.; Sakaguchi, S.; Iwahama, T., Adv. Synth. Catal., 2001, 343, 393.

2. Masui, M.; Hosomi, K.; Tsuchida, K.; Ozaki, S., Chem. Pharm. Bull., 1985, 33, 4798.

3. Martin, J.C.; Taylor, J.W.; Drew, E.H., JACS, 1967, 89, 129.

Sample Availability: Available from MDPI.