Mo(CO)6/TBHP catalyzed autoxidation of 5-alkylidene-4,5-dihydrofurans

Tetrahedron Letters

Volumn 40, Issue 20, 1999, Pages 3899-3902

  Lattanzi, Alessandra ^a   Lannece, Patrizia ^a   Scettri, Arrigo ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; FURAN DERIVATIVE; HYDROPEROXIDE DERIVATIVE;

ARTICLE; AUTOOXIDATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; EPOXIDATION; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033553488     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00564-X     Document Type: Article

References (18)

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9. 6 (1% mol) and TBHP (2 mmol, 5 M solution in decane) at 40-50°C and stirring is maintained until the disappearance of 1 as monitored by TLC. After removal of the solvent in vacuo, flash chromatography of the residue in mixtures of petroleum ether-diethyl ether afforded furyl hydroperoxides 3. Spectroscopic data of 3 are reported in the literature (ref. 5b).
10. 7. (a) Lattanzi, A.; Bonadies, F.; Scettri, A. Tetrahedron: Asymmetry 1997, 8, 2141.
11. (b) For further examples of employment of furyl hydroperoxides in Sharpless type oxidation see: Adam, W.; Korb, M. N. Tetrahedron: Asymmetry 1997, 8, 1131.
12. (c) Adam, W.; Korb, M. N.; Roschmann, K. J., Saha-Möller, C. J. Org. Chem. 1998, 63, 3423.
13. 8. (a) Lattanzi, A.; Bonadies, F.; Senatore, A.; Soriente, A.; Scettri, A. Tetrahedron: Asymmetry 1997, 8, 2473.
14. (b) Lattanzi, A.; Bonadies, F.; Schiavo, A.; Scettri, A. Tetrahedron: Asymmetry 1998, 9, 261 9.
15. 6 induces homolytic decomposition of TBHP, furyl hydroperoxides 3 are unaffected in the mentioned conditions. They are less prone to suffer metal decomposition, probably because of their intrinsic higher chemical stability. For more insight into metal-induced decomposition of primary, secondary and tertiary alkyl hydroperoxides see: Hiatt, R.; Irwin, K. C.; Gould, C. W. J. Org. Chem. 1968, 33, 1430.
16. 10. (a) Barton, D. H. R.; Le Gloahec, V. N.; Patin, H.; Launay, F. New. J. Chem. 1998, 559.
17. (b) Barton, D. H. R.; Le Gloahec, V. N.; Patin New. J. Chem. 1998, 565.
18. 6 (1% mol) and TBHP (2eq.) was conducted in the absence of 1a under air in benzene at 40°C, after 20 h the radical adduct 5 was isolated in 85% yield (based on the phenol).