Conversion of molecular oxygen into a hydroperoxo species by ring- opening protonation of a cyclic η2-peroxo intermediate: Characterization of the η2-peroxo and hydroperoxo complexes

Angewandte Chemie - International Edition

Volumn 38, Issue 20, 1999, Pages 3074-3077

  Takahashi, Yoshiaki ^a   Hashimoto, Mariko ^a   Hikichi, Shiro ^a   Akita, Munetaka ^a   Moro oka, Yoshihiko ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Dioxygen complexes; Hydroperoxo complexes; Oxygenations; Protonations; Rhodium

Indexed keywords

CYTOCHROME P450; HYDROPEROXIDE DERIVATIVE; METAL; METALLOPROTEIN; OXYGEN; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; HYDROGEN BOND; MOLECULAR INTERACTION; OXYGENATION; PROTON TRANSPORT;

EID: 0033581578     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19991018)38:20<3074::AID-ANIE3074>3.0.CO;2-R     Document Type: Article

References (42)

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37. Rh: a) D. Carmona, M. P. Lamata, J. Ferrer, J. Modrego, M. Perales, F. J. Lahoz, R. Atencio, L. A. Oro, J. Chem. Soc. Chem. Commun. 1994,575-576; Co: b) U. Thewalt, R. Marsh, J. Am. Chem. Soc. 1967, 89, 6364-6365; Mo: c) J.-M. Le Carpentier, A. Mitschler, R. Weiss, Acta. Crystallogr. Sect. B 1972, 28, 1288-1290; d) A hydroperoxo- copper complex containing the hydrogen-bonding interaction between the OOH α-oxygen atom and an amido hydrogen atom in the ligand substitutent was recently reported: A. Wada, M. Harata, K. Hasegawa. K. Jitsukawa, H. Masuda, M. Mukai, T. Kitagawa, H. Einaga, Angew. Chem. 1998, 110, 874-875; Angew. Chem. Int. Ed. 1998, 37, 798-799.
38. Rh: a) D. Carmona, M. P. Lamata, J. Ferrer, J. Modrego, M. Perales, F. J. Lahoz, R. Atencio, L. A. Oro, J. Chem. Soc. Chem. Commun. 1994,575-576; Co: b) U. Thewalt, R. Marsh, J. Am. Chem. Soc. 1967, 89, 6364-6365; Mo: c) J.-M. Le Carpentier, A. Mitschler, R. Weiss, Acta. Crystallogr. Sect. B 1972, 28, 1288-1290; d) A hydroperoxo- copper complex containing the hydrogen-bonding interaction between the OOH α-oxygen atom and an amido hydrogen atom in the ligand substitutent was recently reported: A. Wada, M. Harata, K. Hasegawa. K. Jitsukawa, H. Masuda, M. Mukai, T. Kitagawa, H. Einaga, Angew. Chem. 1998, 110, 874-875; Angew. Chem. Int. Ed. 1998, 37, 798-799.
39. Rh: a) D. Carmona, M. P. Lamata, J. Ferrer, J. Modrego, M. Perales, F. J. Lahoz, R. Atencio, L. A. Oro, J. Chem. Soc. Chem. Commun. 1994,575-576; Co: b) U. Thewalt, R. Marsh, J. Am. Chem. Soc. 1967, 89, 6364-6365; Mo: c) J.-M. Le Carpentier, A. Mitschler, R. Weiss, Acta. Crystallogr. Sect. B 1972, 28, 1288-1290; d) A hydroperoxo-copper complex containing the hydrogen-bonding interaction between the OOH α-oxygen atom and an amido hydrogen atom in the ligand substitutent was recently reported: A. Wada, M. Harata, K. Hasegawa. K. Jitsukawa, H. Masuda, M. Mukai, T. Kitagawa, H. Einaga, Angew. Chem. 1998, 110, 874-875; Angew. Chem. Int. Ed. 1998, 37, 798-799.
40. Rh: a) D. Carmona, M. P. Lamata, J. Ferrer, J. Modrego, M. Perales, F. J. Lahoz, R. Atencio, L. A. Oro, J. Chem. Soc. Chem. Commun. 1994,575-576; Co: b) U. Thewalt, R. Marsh, J. Am. Chem. Soc. 1967, 89, 6364-6365; Mo: c) J.-M. Le Carpentier, A. Mitschler, R. Weiss, Acta. Crystallogr. Sect. B 1972, 28, 1288-1290; d) A hydroperoxo- copper complex containing the hydrogen-bonding interaction between the OOH α-oxygen atom and an amido hydrogen atom in the ligand substitutent was recently reported: A. Wada, M. Harata, K. Hasegawa. K. Jitsukawa, H. Masuda, M. Mukai, T. Kitagawa, H. Einaga, Angew. Chem. 1998, 110, 874-875; Angew. Chem. Int. Ed. 1998, 37, 798-799.
41. Because X-ray crystallography suggested intermolecular hydrogen-bonding interactions (O2 ⋯ N42*: 2.978(9) Å, O2 ⋯ N52*: 2.92(1)Å), location of the hydrogen atoms would be disordered among the O and N atoms. Another possible structure with mirror symmetry contains one hydrogen atom in the middle of the O2, N42, and N52 atoms and the other bonded only to the O2 atom, but apparently it is not consistent with the spectral data.
42. The formation of 3 is an irreversible process.