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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 24, 1994 - Issue 20
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Original Articles

Synthesis of 1,2-Epoxy-1,2,3,4-Tetrahydrobenzo[g]chrysene: The First Synthesis of a FJORD-Region Tetrahydroepoxide

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Pages 2973-2981 | Received 07 Apr 1994, Published online: 23 Sep 2006

References

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  • Phenanthrene is prototypical of hydrocarbons that contain a “bay-region”, which is the sterically congested region between C-4 and C-5 of this hydrocarbon
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  • 1H NMR (300 MHz, CDCl3) of 7: 2.47 (quint, 2H3, Japp = 6.7); 3.00 (t, 2H2, Japp = 6.8); 3.40 (t, 2H4, Japp = 6.7); 7.40–7.60 (m, 2H6,7); 7.70 (t, 1H12, J = 7.3); 7.80 (t, 1H13, J = 7.3); 7.92 (d, 1H5, J = 7.6); 8.00 (d, 1H10, J = 8.6); 8.10 (d, 1H8, J = 8.6); 8.23 (d, 1H11, J = 8.6); 8.60 (d, 1H9, J = 8.6); 8.74 (d, 1H14, J = 7.3)
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  • 1H NMR of 3,4-dihydrobenzo[g]chrysen-2(1H)-one: 2.60 (t, 2H3, Japp = 9.5); 3.75 (t, 2H4, Japp = 9.5); 4.55 (s, 2H1); 7.60–7.80 (m, 4H6,7,12,13); 8.00 (m, 2H10,11); 8.35–8.42 (m, 2H5,8); 8.66 (d, 1H9, J = 9.1); 8.83 (m, 1H14)
  • Schurdak , M. E. , Chang , R. L. , Conney , A. H. , Grossman , S. , Jerina , D. M. , Bushman , D. R. , Utermoehlen , C. M. , Singh , M. , Lehr , R. E. and Wood , A. W. presented at the Eightieth Annual meeting of the American Association for Cancer Research . Genotoxic activity of benzo[g]chrysene and several of its known or potential metabolites
  • Wood , A. W. Dr. Roche Institute of Molecular Biology , New Jersey : Nutley . Biological testing was performed in the laboratory of

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