A novel catalyzed C-H insertion reactions of hydrogen peroxide by poly(4-vinylpyridine)/methyltrioxorhenium systems

Tetrahedron Letters

Volumn 45, Issue 11, 2004, Pages 2351-2353

  Bianchini, Gianluca ^a   Crucianelli, Marcello ^a   De Angelis, Francesco ^a   Neri, Veronica ^b   Saladino, Raffaele ^b  

^a UNIVERSITY OF L'AQUILA   (Italy)

^b UNIVERSITY OF TUSCIA   (Italy)

Author keywords

C H insertion reaction; Heterogeneous catalysis; Hydrogen peroxide; Methyltrioxorhenium

Indexed keywords

HYDROCARBON; HYDROGEN PEROXIDE; METHYLTRIOXORHENIUM; POLY(4 VINYLPYRIDINE); PYRIDINE DERIVATIVE; RHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; OXIDATION; REACTION ANALYSIS;

INSERTION SEQUENCES;

EID: 1242338134     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.083     Document Type: Article

References (16)

1. 2 oxidation of hydrocarbons, see: Shul'pin G.B. Comptes Rendus Chimie. 6:2003;163-178.
2. Nizova G.V., Bolm C., Ceccarelli S., Pavan C., Shul'pin G.B. Adv. Synth. Catal. 344:2002;899-905.
3. For general reviews, see: Romão C.C., Kühn F.E., Herrmann W.A. Chem. Rev. 97:1997;3197-3246.
4. Owens G.S., Arias J., Abu-Omar M.M. Catal. Today. 55:2000;317-363.
5. Herrmann W.A., Fischer R.W., Scherer W., Rouch M.U. Angew. Chem., Int. Ed. Engl. 32:1993;1157-1160.
6. Murray R.W., Iyanar K., Chen J., Wearing J.T. Tetrahedron Lett. 36:1995;6415-6418.
7. Schuchardt U., Mandelli D., Shul'pin G.B. Tetrahedron Lett. 37:1996;6487-6490.
8. Saladino R., Neri V., Pelliccia A.R., Caminiti R., Sadun C. J. Org. Chem. 67:2002;1323-1332.
9. Saladino R., Neri V., Mincione E., Filippine P. Tetrahedron. 58:2002;8493-8500.
10. Saladino R., Mincione E., Attanasi O.A., Filippone P. Pure Appl. Chem. 75:2003;261-268.
11. Saladino R., Neri V., Pelliccia A.R., Mincione E. Tetrahedron. 59:2003;7403-7408.
12. Bernini R., Mincione E., Cortese M., Saladino R., Gualandi G., Belfiore M.C. Tetrahedron Lett. 44:2003;4823-4825.
13. Compounds I and II were prepared as reported in Ref. 6. In summary, MTO (256 mg, 1.0 mmol) was added to a suspension of the appropriate resin (1.0 g) in ethanol (4 mL). The mixture was stirred for 1 h using a magnetic stirrer. The solvent was removed by filtration, and the catalyst was washed with ethyl acetate and finally dried under high vacuum.
14. The reaction mixtures have been analyzed by a Hewlett Packard 6890 Series gas chromatograph equipped with a FID, using a 30 m × 0.32 mm × 0.25 μm film thickness (cross-linked 5% phenylmethylsiloxane) column and nitrogen as carrier gas. The identification of the peaks by GC-MS has been performed by means of a Varian 2000 GC-MAS instrument, using the same column. Yields and conversions of the reactions have been quantified using n-octane as internal standard, or when necessary, after chromatographic purification.
15. See for recent examples: Revital B.D., Ronny N. Angew. Chem., Int. Ed. Engl. 42:2003;92-95.
16. Ishii Y., Nakayama K., Takeno M., Sakaguchi S., Iwahama T., Nishiyama Y. J. Org. Chem. 60:1995;3934-3935.