A Convenient New Synthesis of Benzo[a]pyrene

Journal of Organic Chemistry

Volumn 69, Issue 4, 2004, Pages 1372-1373

  Harvey, Ronald G ^a   Lim, Keunpoong ^a   Dai, Qing ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; BENZENE; NAPHTHALENE; ORGANIC ACIDS;

SUZUKI COUPLINGS;

SYNTHESIS (CHEMICAL);

2 BROMOBENZENE 1,3 DIALDEHYDE; ALDEHYDE DERIVATIVE; BENZENE DERIVATIVE; BENZO[A]PYRENE; BORONIC ACID DERIVATIVE; CARCINOGEN; NAPHTHALENE 2 BORONIC ACID; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUZUKI REACTION; SYNTHESIS; WITTIG REACTION;

BENZO(A)PYRENE; CARCINOGENS, ENVIRONMENTAL; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; REFERENCE STANDARDS;

EID: 1242352430     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030313n     Document Type: Article

References (17)

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5. Denissenko, M. F.; Pao, A.; Tang, M.; Pfeifer, G. P. Science 1996, 274, 430. Pfeifer, G. P.; Denissenko, M. F. Environ. Mol. Carcin. 1998, 31, 197. Denissenko, M. F.; Chen, J. X.; Tang, M.; Pfeifer, G. P. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 3893. Chen, J. X.; Zheng, Y.; West, M.; Tang, M. Cancer Res. 1998, 58, 2170.
6. Denissenko, M. F.; Pao, A.; Tang, M.; Pfeifer, G. P. Science 1996, 274, 430. Pfeifer, G. P.; Denissenko, M. F. Environ. Mol. Carcin. 1998, 31, 197. Denissenko, M. F.; Chen, J. X.; Tang, M.; Pfeifer, G. P. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 3893. Chen, J. X.; Zheng, Y.; West, M.; Tang, M. Cancer Res. 1998, 58, 2170.
7. Denissenko, M. F.; Pao, A.; Tang, M.; Pfeifer, G. P. Science 1996, 274, 430. Pfeifer, G. P.; Denissenko, M. F. Environ. Mol. Carcin. 1998, 31, 197. Denissenko, M. F.; Chen, J. X.; Tang, M.; Pfeifer, G. P. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 3893. Chen, J. X.; Zheng, Y.; West, M.; Tang, M. Cancer Res. 1998, 58, 2170.
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11. Johnson, W. S. Org. React. 1944, 2, 114. Schlude, H. Chem. Ber. 1971, 104, 3995. Cook, J. W.; Hewett, C. L. J. Chem. Soc. 1933, 398.
12. Method employed is based on the procedure reported: Zhang, F.-J.; Cortez, C.; Harvey, R. G. J. Org. Chem. 2000, 65, 3952. The use of Suzuki coupling for the synthesis of PAH compounds has also been described by: Kumar, S. J. Chem. Soc., Perkin Trans. 1 1998, 3157.
13. Method employed is based on the procedure reported: Zhang, F.-J.; Cortez, C.; Harvey, R. G. J. Org. Chem. 2000, 65, 3952. The use of Suzuki coupling for the synthesis of PAH compounds has also been described by: Kumar, S. J. Chem. Soc., Perkin Trans. 1 1998, 3157.
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16. An improved procedure for the synthesis of 2 is described in: Harvey, R. G.; Dai, Q.; Ran, C.; Penning, T. M. J. Org. Chem., in press.
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