Conversion of 1,2‐Diols into Aldehydes Induced by Photolysis of Alkylcobaloximes: A Model System for Dioldehydrase
1975; Wiley; Volume: 14; Issue: 12 Linguagem: Inglês
10.1002/anie.197508131
ISSN1521-3773
AutoresBernard T. Golding, Terence J. Kemp, Enrico Nocchi, William P. Watson,
Tópico(s)Metalloenzymes and iron-sulfur proteins
ResumoAngewandte Chemie International Edition in EnglishVolume 14, Issue 12 p. 813-814 Communication Conversion of 1,2-Diols into Aldehydes Induced by Photolysis of Alkylcobaloximes: A Model System for Dioldehydrase† Dr. Bernard T. Golding, Corresponding Author Dr. Bernard T. Golding Department of Molecular Sciences, University of Warwick, Coventry CV4 7AL (England)Department of Molecular Sciences, University of Warwick, Coventry CV4 7AL (England)Search for more papers by this authorDr. Terence J. Kemp, Dr. Terence J. Kemp Department of Molecular Sciences, University of Warwick, Coventry CV4 7AL (England)Search for more papers by this authorDr. Enrico Nocchi, Dr. Enrico Nocchi Department of Molecular Sciences, University of Warwick, Coventry CV4 7AL (England)Search for more papers by this authorDr. William P. Watson, Dr. William P. Watson Department of Molecular Sciences, University of Warwick, Coventry CV4 7AL (England)Search for more papers by this author Dr. Bernard T. Golding, Corresponding Author Dr. Bernard T. Golding Department of Molecular Sciences, University of Warwick, Coventry CV4 7AL (England)Department of Molecular Sciences, University of Warwick, Coventry CV4 7AL (England)Search for more papers by this authorDr. Terence J. Kemp, Dr. Terence J. Kemp Department of Molecular Sciences, University of Warwick, Coventry CV4 7AL (England)Search for more papers by this authorDr. Enrico Nocchi, Dr. Enrico Nocchi Department of Molecular Sciences, University of Warwick, Coventry CV4 7AL (England)Search for more papers by this authorDr. William P. Watson, Dr. William P. Watson Department of Molecular Sciences, University of Warwick, Coventry CV4 7AL (England)Search for more papers by this author First published: December 1975 https://doi.org/10.1002/anie.197508131Citations: 12 † Financial support was given by the Science Research Council (to W. P. W.) and by the Academia Nazionale dei Lincei (to E. N. under the auspices of the Royal Society European Exchange Scheme).—We acknowledge excellent technical assistance from L. C. Carr and G. Noon. 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 No abstract is available for this article. References 1 Cf. H. A. Barker, Annu. Rev. Biochem. 41, 55 (1972). 2 T. H. Finlay, J. Valinsky, K. Sato, and R. H. Abeles, J. Biol. Chem. 247, 4197 (1972). 3 B. T. Golding and L. Radom, J. Chem. Soc. Chem. Commun. 1973, 939. 4(a) B. C. Gilbert, J. P. Larkin, and R. O. C. Norman, J. Chem. Soc. Perkin II 1972, 794: (b) K. M. Bansal, M. Grätzel, A. Henglein, and E. Janata, J. Phys. Chem. 77, 16 (1973): (c) C. Walling and R. A. Johnson, J. Am. Chem. Soc. 97, 2405 (1975). 5 Alkyl(base) cobaloximes are bis(biacetyldioximato)cobalt complexes with a σ-alkyl group and a Lewis base as axial ligands, used as models for alkylcobalamins [cf. G. N. Schrauzer, Acc. Chem. Res. 1, 97 (1968)]. Syntheses of (1) and (2): B. T. Golding et al., to be published. 6 In the control experiments mentioned, ≥ 0.2% yield (based on cobaloxime) of acetaldehyde or pentanal would have been detected. 7 J. W. Wilt in J. K. Kochi: Free Radicals. Wiley-Interscience, New York 1973, Vol. 1, Chap. 8, p. 380. 8 See, however, T. Yamane, S. Shimizu, and S. Fukui, Biochim. Biophys. Acta 110, 616 (1965). 9 1,4-Hydrogen transfer in the 4,5-dihydroxypentyl radical giving the radical \documentclass{article}\usepackage{amssymb}\pagestyle{empty}\begin{document}$n\hbox{-C}_3{\rm H}_7\mathop {\rm C}\limits^\bullet{\rm OHCH}_2{\rm OH}$\end{document}, followed by acid-catalyzed rearrangement[4a] would yield 2-pentanone which was not detected after photolysis of (2). Citing Literature Volume14, Issue12December 1975Pages 813-814 ReferencesRelatedInformation
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