Preparation and complete 1 H and 13C assignment of some pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione (PCUD) derivatives
Corresponding Author
Alan M. Kenwright
Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, UK
Alan M. Kenwright and Jonathan D. Sellars, Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, DH1 3LE, UK. E-mail: [email protected]; E-mail: [email protected]Search for more papers by this authorCorresponding Author
Jonathan D. Sellars
Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, UK
Alan M. Kenwright and Jonathan D. Sellars, Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, DH1 3LE, UK. E-mail: [email protected]; E-mail: [email protected]Search for more papers by this authorCorresponding Author
Alan M. Kenwright
Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, UK
Alan M. Kenwright and Jonathan D. Sellars, Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, DH1 3LE, UK. E-mail: [email protected]; E-mail: [email protected]Search for more papers by this authorCorresponding Author
Jonathan D. Sellars
Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, UK
Alan M. Kenwright and Jonathan D. Sellars, Department of Chemistry, University of Durham, Science Laboratories, South Road, Durham, DH1 3LE, UK. E-mail: [email protected]; E-mail: [email protected]Search for more papers by this authorAbstract
The preparation of a number of alkyl and alkoxy derivatives of pentacyclo[5.4.0.02,6.03,10.05,9]undecane-8,11-dione derivatives utilising a cheap, practical, low energy, ‘green’, single-pass continuous flow photochemical reactor is reported. Their 1 H and 13C NMR spectra are fully assigned, revealing some general characteristics not previously reported for this class of compound, which should aid the assignment and prediction of the NMR spectra of PCUD derivatives. Copyright © 2012 John Wiley & Sons, Ltd.
Supporting Information
Electronic supplementary information (ESI) available: 1 H and 13C NMR assignments and spectra for all compounds, construction of the flow reactor, absorbance profile versus reactor emission profile, and the rate of conversion of 1 t to 1p.
| Filename | Description |
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| mrc_3879_suplementary_material_figures.docxWord 2007 document , 1.4 MB | Supporting Information |
| mrc_3879_suplementary_material_spectra.pdfPDF document, 684.9 KB | Supporting Information |
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References
- 1 R. C. Cookson, E. Crundwell, R. R. Hill, J. Hudec. J. Chem. Soc. (Resumed) 1964, 3062–3075.
- 2 A. P. Marchand, in Advances in Theoretically Interesting Molecules Volume 1 (Ed: R. P. Thummel), JAI Press Inc., London, 1989, pp. 357–399.
- 3 A. P. Marchand, S. C. Suri, A. D. Earlywine, D. R. Powell, D. Vanderhelm. J. Org. Chem. 1984, 49, 670–675.
- 4 W. J. Geldenhuys, S. F. Malan, J. R. Bloomquist, A. P. Marchand, C. J. Van der Schyf. Med. Res. Rev. 2005, 25, 21–48.
- 5 G. Mehta, A. V. Reddy. J. Chem. Soc., Chem. Commun. 1981, 756–757.
- 6 G. Mehta, A. Srikrishna, A. Reddy, M. Nair. Tetrahedron 1981, 37, 4543–4559.
- 7 O. K. Onajole, Y. Coovadia, T. Govender, H. G. Kruger, G. E. M. Maguire, D. Naidu, N. Singh, P. Govender. Chem. Biol. Drug Des. 2011, 77, 295–299.
- 8 M. M. Makatini, K. Petzold, S. N. Sriharsha, M. E. S. Soliman, B. Honarparvar, P. I. Arvidsson, Y. Sayed, P. Govender, G. E. M. Maguire, H. G. Kruger, T. Govender. Bioorg. Med. Chem. Lett. 2011, 21, 2274–2277.
- 9 S. De Jonghe, A. Marchand, L.-J. Gao, A. Calleja, E. Cuveliers, I. Sienaert, J. Herman, G. Clydesdale, H. Sefrioui, Y. Lin, W. Pfleiderer, M. Waer, P. Herdewijn. Bioorg. Med. Chem. Lett. 2011, 21, 145–149.
- 10 G. A. Boyle, T. Govender, H. G. Kruger, G. E. M. Maguire, T. Naicker. Struct. Chem. 2008, 19, 429–434.
- 11 O. K. Onajole, P. Govender, T. Govender, G. E. M. Maguire, H. G. Kruger. Struct. Chem. 2009, 20, 1067–1076.
- 12 O. K. Onajole, M. M. Makatini, P. Govender, T. Govender, G. E. M. Maguire, H. G. Kruger, Magn. Reson. Chem. 2010, 48, 249–255.
- 13 J. Joubert, W. J. Geldenhuys, C. J. Van der Schyf, D. W. Oliver, H. G. Kruger, T. Govender, S. F. Malan. ChemMedChem 2012, 7, 375–384.
- 14 B. D. A. Hook, W. Dohle, P. R. Hirst, M. Pickworth, M. B. Berry, K. I. Booker-Milburn. J. Org. Chem. 2005, 70, 7558–7564.
- 15 A. Sugimoto, T. Fukuyama, Y. Sumino, M. Takagi, I. Ryu. Tetrahedron 2009, 65, 1593–1598.
- 16 In all cases the numbering used in discussion of the shifts follows the standard IUPAC numbering for the ring systems in the parent compounds.
- 17
K. B. Wiberg, in The Chemistry of Cyclobutanes (PATAI'S Chemistry of Functional Groups), (Eds: Z. Rappoport, J. F. Liebman). Wiley-Blackwell, 2005, pp. 1–15.
10.1002/0470864028.ch1 Google Scholar
- 18 D. M. Grant, E. G. Paul. J. Am. Chem. Soc. 1964, 86, 2984–2990.
- 19 D. K. Dalling, D. M. Grant. J. Am. Chem. Soc. 1974, 96, 1827–1834.
- 20 D. K. Dalling, D. M. Grant, E. G. Paul. J. Am. Chem. Soc. 1973, 95, 3718–3724.
- 21 P. E. Hansen. Prog. Nucl. Magn. Reson. Spectrosc. 1981, 14, 175–295.
- 22 T. Axenrod, B. Liang, A. Bashir-Hashemi, P. R. Dave, D. S. Reddy. Magn. Reson. Chem. 1991, 29, 88–91.
- 23 J. J. Burke, P. C. Lauterbur. J. Am. Chem. Soc. 1964, 86, 1870–1871.
- 24 NMR Predict, Modgraph Consultants Ltd, Version 4.8.
- 25 D. H. Cadd, W. J. Feast, A. M. Kenwright, J. M. Say. Magn. Reson. Chem. 1993, 31, 801–807.
- 26 H. G. Kruger, R. Ramdhani. Magn. Reson. Chem. 2006, 44, 1058–1062.
- 27 G. Tolstikov, B. Lerman, F. Galin, Y. Struchkov, V, Andrianov, Tetrahedron Lett, 1978, pp. 4145–4148.
- 28 G. Mehta, D. Reddy, A. Reddy. Tetrahedron Lett. 1984, 25, 2275–2278.
- 29 V. S. Watts. J. Chem. Phys. 1967, 46, 4165–4166.
- 30 S. Berger, in The Chemistry of Alkanes and Cycloalkanes (PATAI's Chemistry of Functional Groups) (Eds: S. Patai, Z. Rappoport), Wiley-Blackwell, London, 1992, pp. 351–389.
- 31 T. J. Katz, N. Acton. J. Am. Chem. Soc. 1973, 95, 2738–2739.
- 32
R. J. Abraham,
M. A. Warne,
L. Griffiths. J. Chem. Soc., Perkin Trans. 1997, 2, 31–40.
10.1039/a604567g Google Scholar
- 33 P. E. Eaton, Y. S. Or, S. J. Branca, B. K. Ravi Shankar. Tetrahedron 1986, 42, 1621–1631.
