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Polycyclic Aromatic Compounds Volume 5, 1995 - Issue 1-4
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Synthesis, Physico-Chemical and Spectroscopic Properties of PAC and Metabolites

Synthesis and Reactions of Methylene-bridged Polycyclic Aromatic Hydrocarbons

Ronald G. Harvey Ben May Institute, University of Chicago, Chicago, Illinois, 60637
,
Chengxi Yang Ben May Institute, University of Chicago, Chicago, Illinois, 60637
&
Elias Abu-shqara Ben May Institute, University of Chicago, Chicago, Illinois, 60637
Pages 35-42 | Published online: 22 Sep 2006

References

  • Adams , J. D. , LaVoie , E. J. and Hoffmann , D. 1982 . J. Chromatogr. Sci. , 20 : 274
  • Blumer , M. 1976 . Sci. Am. , 234 : 35
  • Rice , J. , Jordan , K. , Little , P. and Hussein , N. 1988 . Carcinogenesis , 9 : 2275
  • Yang , C. and Harvey , R. G. 1992 . Tetrahedron , 48 : 3775
  • Glatt , H. , Henschler , R. , Frank , H. , Seidel , A. , Yang , C. , Abu-shqara , E. and Harvey , R. G. 1993 . Carcinogenesis , 14 : 599
  • Harvey , R. G. 1991 . Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenicity , Cambridge, , England : Cambridge University Press .
  • Yang , C. and Harvey , R. G. 1992 . Polycyclic Arom. Compds. , 2 : 239
  • Ray , J. and Harvey , R. G. 1983 . J. Org. Chem. , 48 : 1352
  • Harvey , R. G. , Pataki , J. , Cortez , C. , DiRaddo , P. and Yang , C. 1991 . J. Org. Chem. , 56 : 1210
  • Young , R. J. and Harvey , R. G. 1989 . Tetrahedron Lett. , 30 : 6603
  • Yang , C. , Yang , D. T. C. and Harvey , R. G. 1992 . Synlett. , : 799
  • Compound 14 was a pale yellow solid: mp 182–183°C; NMR δ 9. 44 (d, 1, H11 J =8. 5 Hz), 9. 29 (d, 1, H12 J =9. 1 Hz), 7. 68–8. 14 (m, 10, Ar), 4. 52 (s, 2, CH2); UVλmax (EtOH) 318 (ε 9 955), 307 (23 180), 279 (70 910), 207 (32 730) nm
  • Compound 19 was obtained as white needles: mp 266–267°C; NMR δ 8. 69 (d, 2, H1, 11 J =7. 9 Hz), 8. 64 (s, 2, H12, 13), 8. 01 (d, 2, H4, 8; J =7. 8 Hz), 7. 89 (s, 2, H5, 7), 7. 68 (t, 2, H2, 10 J=7. 6 Hz), 7. 65 (t, 2, H3, 9 J=7. 5 Hz), 4. 51 (s, 2, CH2); UVλmax (EtOH) 332 (ε 21 000), 303 (24 400), 283 (89 300), 252 (54 400), 227 (22 900), 191 (23 800) nm
  • Karcher , W. 1988 . Spectral Atlas of Polycyclic Aromatic Compounds , Vol. 2 , Dordrecht, , Netherlands : Kluwer Academic Publishers .
  • Compound 22 was obtained as pale yellow crystals: mp 207–208°C; NMR δ 8. 22 (d, 2, H1, 12J =8. 8 Hz), 8. 19 (s, 2, H5, 8), 8. 12 (d, 2, H4, 9; J=8. 2 Hz), 7. 70 (s, 2, H6, 7), 7. 60 (t, 2, H3, 10J=7. 6 Hz), 7. 53 (t, 2, H2, 11J=7. 5 Hz), 4. 78 (s, 2, CH2); UVλmax (EtOH) 362 (ε 24 000), 343 (25 000), 330 (34 700), 314 (45 000), 258 (87 400), 226 (60 700), 195 (25 900) nm. Compound 23 melted at 243. 5–244. 5°C; NMR δ 8. 62 (d, 1, H4J =8. 0 Hz), 8. 45 (d, 1, H5J =9. 0 Hz), 8. 38 (s, 1, H7), 8. 18 (m, 2, Ar, J =8. 7 Hz), 8. 05 (m, 3, Ar), 7. 66 (t, 1, Ar), 7. 59 (m, 2, Ar), 7. 52 (m, 1, Ar), 4. 73 (s, 2, CH2); UVλmax (EtOH) 395 (ε 8750), 373(9890), 353(7200), 334(5560), 288 (99 400), 244 (40 100), 200 (24 500), 192 (20 600) nm.
  • Minabe , M. , Cho , B. and Harvey , R. G. 1989 . J. Am. Chem. Soc. , 111 : 3809
  • Tetrabenzo[de, hi, mn, qr]naphthacene was obtained as pale yellow needles, mp 306 308°C (lit.18 305–307°C); NMR δ 9. 21 (d, 4, H1, 8, 9, 16 J =7. 8 Hz), 8. 23 (d, 4, H3, 6, 11, 14 J =7. 2 Hz), 8. 14 (s, 4, H4, 5, 12, 13), 8. 05 (t, 4, H2, 7, 10, 15 J =7. 8 Hz)
  • Clar , E. , Guye-Villème , J. F. and Stephen , J. F. 1964 . Tetrahedron , 20 : 2107

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