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A General and Efficient Method for the Monohydroxylation of Alkanes

1996; Wiley; Volume: 35; Issue: 2 Linguagem: Inglês

10.1002/anie.199602171

ISSN

1521-3773

Autores

Gregorio Asensio, Rossella Mello, María Elena González‐Núñez, Gloria Castellano, Julia Corral,

Tópico(s)

Synthesis and Catalytic Reactions

Resumo

Angewandte Chemie International Edition in EnglishVolume 35, Issue 2 p. 217-218 Communication A General and Efficient Method for the Monohydroxylation of Alkanes† Prof. Dr. Gregorio Asensio, Corresponding Author Prof. Dr. Gregorio Asensio Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Search for more papers by this authorDr. Rossella Mello, Dr. Rossella Mello Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Search for more papers by this authorProf. Dr. María Elena González-Núñnez, Prof. Dr. María Elena González-Núñnez Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Search for more papers by this authorGloria Castellano, Gloria Castellano Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Search for more papers by this authorJulia Corral, Julia Corral Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Search for more papers by this author Prof. Dr. Gregorio Asensio, Corresponding Author Prof. Dr. Gregorio Asensio Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Search for more papers by this authorDr. Rossella Mello, Dr. Rossella Mello Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Search for more papers by this authorProf. Dr. María Elena González-Núñnez, Prof. Dr. María Elena González-Núñnez Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Search for more papers by this authorGloria Castellano, Gloria Castellano Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Search for more papers by this authorJulia Corral, Julia Corral Departamento de Química Orgánica, Facultad de Farmacia Universidad de Valencia Avda. Vicente Andrés Estellés s.n., E-46100 Burjassot, Valencia (Spain) Fax: Int. code +(6)386-4939Search for more papers by this author First published: February 2, 1996 https://doi.org/10.1002/anie.199602171Citations: 25 † This work was supported by the Spanish Directión General de Investigación Cientifica y Técnica (PB93-0681). We thank the S. C. S. I. E. Universidad de Valencia for the use of NMR and GC-MS facilities. AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Graphical Abstract The initially formed alcohols do not oxidize further when primary and secondary C-H bonds are oxidized by dioxirane 1 in the presence of a large excess of trifluoroacetic anhydride. The reactions (a) proceed with excellent yields under very mild conditions. R = alkyl, aryl; R′ = H, alkyl, aryl. References 1(a) O. Reiser, Angew. Chem. 1994, 106, 73; Angew. Chem. Int. Ed. Engl. 1994, 33, 69; (b) D. H. R. Barton, D. Doller, Acc. Chem. Res. 1992, 25, 504; (c) B. Meunier, Chem. Rev. 1992, 92, 1411; (d) J. F. Larrow, E. N. Jacobsen, J. Am. Chem. Soc. 1994, 116, 12129; (e) K. Nomura, S. Uemura, J. Chem. Soc. Chem. Commun. 1994, 129; (f) A. Tenaglia, E. Terranova, B. Waegell, Tetrahedron Lett. 1989, 30, 5271; (g) P. H. J. Carlsen, Synth. Commun. 1987, 17, 19; (h) D. D. Desmarteu, A. Donadelli, V. Montanari, V. A. Petrov, G. Resnati, J. Am. Chem. Soc. 1993, 115, 4897; (i) M. D. Kaufman, P. A. Grieco, D. W. Bougie, J. Am. Chem. Soc. 1993, 115, 11648; (j) A. de Meijere, F. Wolf, Methoden Org. Chem. (Houben-Weyl) 4th ed. 1952, E13, 1988, pp. 971–990, and references therein; (k) G. A. Olah, G. K. S. Prakash, J. Sommer, Superacids, Wiley, New York, 1985, and references therein. 2 R. Mello, M. Fiorentino, C. Fusco, R. Curci, J. Am. Chem. Soc. 1989, 111, 6749. 3 R. Mello, L. Cassidei, M. Fiorentino, C. Fusco, W. Hümmer, V. Jäger, R. Curci, J. Am. Chem. Soc. 1991, 113, 2205. 4(a) D. Kuck, A. Schuster, C. Fusco, M. Fiorentino, R. Curci, J. Am. Chem. Soc. 1994, 116, 2375; (b) G. D. Maynard, L. A. Paquette, J. Org. Chem. 1991, 56, 5480. 5 W. Adam, M. E. González-Núñez, R. Mello, R. Curci, J. Am. Chem. Soc. 1991, 113, 7654. 6 R. D. Bach, M.-D. Su, J. Am. Chem. Soc. 1994, 116, 10103. 7(a) D. H. Giamalva, D. F. Church, W. A. Pryor, J. Org. Chem. 1988, 53, 3429; (b) J. Am. Chem. Soc. 1986, 108, 7679. 8 W. Adam, G. Asensio, R. Curci, M. E. González-Núñez, R. Mello, J. Am. Chem. Soc. 1992, 114, 8345. Citing Literature Volume35, Issue2February 2, 1996Pages 217-218 ReferencesRelatedInformation

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