Migration of redundant ethynyl substituents along polycyclic aromatic hydrocarbon peripheries. Consequences for polycyclic aromatic hydrocarbon build up

Tetrahedron Letters

Volumn 38, Issue 41, 1997, Pages 7255-7258

  Sarobe, Martin ^a   Jenneskens, Leonardus W ^a   Kleij, Arjan ^a   Petroutsa, Maria ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030724977     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01685-7     Document Type: Article

References (20)

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2. Bockborn, H.; Fetting, F.; Wenz, H. Ber. Bunsenges. Phys. Chem., 1983, 87, 1067; Lafleur, A.L.; Gagel, J.J.; Longwell, J.P.; Monchamp, P.A. Energy & Fuels, 1988, 2, 709 and references cited.
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4. For reviews: Jenneskens, L.W.; Sarobe, M.; Zwikker, J.W. Pure & Appl. Chem., 1996, 68, 219 and references cited; Scott, L.W. Pure & Appl. Chem., 1996, 68, 291 and references cited; Rabideau, P.W.; Sygula, A. Acc. Chem. Res., 1996, 29, 235 and references cited.
5. For reviews: Jenneskens, L.W.; Sarobe, M.; Zwikker, J.W. Pure & Appl. Chem., 1996, 68, 219 and references cited; Scott, L.W. Pure & Appl. Chem., 1996, 68, 291 and references cited; Rabideau, P.W.; Sygula, A. Acc. Chem. Res., 1996, 29, 235 and references cited.
6. o): cyclopenta[cd]fluoranthene: Sarobe, M.; Snoeijer, J.D.; Jenneskens, L.W.; Slagt, M.Q.; Zwikker, J.W. Tetrahedron Lett., 1995, 36, 8489; pyracylene: Sarobe, M.; Flink, S.; Jenneskens, L.W.; Zwikker, J.W.; Wesseling, J. J. Chem. Soc., Perkin Trans. 2, 1996, 2125.; benzo[d]pyracylene: Scott, L.T.; Necula, A. Tetrahedron Lett., 1997, 38, 1877; see also Brown, R.F.C.; Eastwood, F.W.; Wong, N.R. Tetrahedron Lett., 1993, 34, 1223.
7. o): cyclopenta[cd]fluoranthene: Sarobe, M.; Snoeijer, J.D.; Jenneskens, L.W.; Slagt, M.Q.; Zwikker, J.W. Tetrahedron Lett., 1995, 36, 8489; pyracylene: Sarobe, M.; Flink, S.; Jenneskens, L.W.; Zwikker, J.W.; Wesseling, J. J. Chem. Soc., Perkin Trans. 2, 1996, 2125.; benzo[d]pyracylene: Scott, L.T.; Necula, A. Tetrahedron Lett., 1997, 38, 1877; see also Brown, R.F.C.; Eastwood, F.W.; Wong, N.R. Tetrahedron Lett., 1993, 34, 1223.
8. o): cyclopenta[cd]fluoranthene: Sarobe, M.; Snoeijer, J.D.; Jenneskens, L.W.; Slagt, M.Q.; Zwikker, J.W. Tetrahedron Lett., 1995, 36, 8489; pyracylene: Sarobe, M.; Flink, S.; Jenneskens, L.W.; Zwikker, J.W.; Wesseling, J. J. Chem. Soc., Perkin Trans. 2, 1996, 2125.; benzo[d]pyracylene: Scott, L.T.; Necula, A. Tetrahedron Lett., 1997, 38, 1877; see also Brown, R.F.C.; Eastwood, F.W.; Wong, N.R. Tetrahedron Lett., 1993, 34, 1223.
9. o): cyclopenta[cd]fluoranthene: Sarobe, M.; Snoeijer, J.D.; Jenneskens, L.W.; Slagt, M.Q.; Zwikker, J.W. Tetrahedron Lett., 1995, 36, 8489; pyracylene: Sarobe, M.; Flink, S.; Jenneskens, L.W.; Zwikker, J.W.; Wesseling, J. J. Chem. Soc., Perkin Trans. 2, 1996, 2125.; benzo[d]pyracylene: Scott, L.T.; Necula, A. Tetrahedron Lett., 1997, 38, 1877; see also Brown, R.F.C.; Eastwood, F.W.; Wong, N.R. Tetrahedron Lett., 1993, 34, 1223.
10. Brown, R.F.C.; Coulston, K.J.; Eastwood, F.W. Tetrahedron Lett., 1996, 37, 6819.
11. 10 226.0782, found 226.0778.
12. 10 226.0782, found 226.0779.
13. 2
14. Sarobe, M.; Zwikker, J.W.; Snoeijer, J.D.; Wiersum, U.E.; Jenneskens, L.W. J. Chem. Soc., Chem. Commun., 1994, 89 and references cited.
15. Sarobe, M.; Jenneskens, L.W.; Wiersum, U.E. Tetrahedron Lett., 1996, 37, 1121 and references cited.
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17. See also: Hofmann, J.; Zimmermann, G.; Findeisen, M. Tetrahedron Lett., 1995, 36, 3831.
18. -1): 2 (142.5) - (TS; 221.1) -> 14 (203.5) - (TS; 250.6) -> 15 (177.8) - (TS; 250.6) -> 16 (204.0) - (TS; 220.5) -> 6 (116.6) with TS being the transition state; see also Scheme 2.
19. Schultz, J.; Goldberg, M.A.; Ordas, E.P.; Carsch, G. J. Org. Chem., 1946, 11, 307.
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