Regioselective Oxidations of Benzocarbaporphyrins with Ferric Chloride: A Facile Synthesis of Bridged [18]Annulene Ketals with Strong Absorptions in the Far Red and an Unexpected Halogenation Reaction at the Interior Carbon Atom

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8558-8570

  Lash, Timothy D ^a   Muckey, Melanie A ^a   Hayes, Michael J ^a   Liu, Dachun ^a   Spence, John D ^a,b   Ferrence, Gregory M ^a  

^a ILLINOIS STATE UNIVERSITY   (United States)

^b TRINITY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; OXIDATION; SUBSTITUTION REACTIONS;

REGIOSELECTIVE OXIDATIONS;

AROMATIC HYDROCARBONS;

2 PROPANOL; ACETAL; ALCOHOL; ANNULENE DERIVATIVE; BENZOCARBAPORPHYRIN; CARBON; CHLORINE; ETHYLENE GLYCOL; FERRIC CHLORIDE; INDENE DERIVATIVE; METHANOL; PORPHYRIN DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION; ARTICLE; CHEMICAL REACTION; HALOGENATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

EID: 0142165944     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030127h     Document Type: Article

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36. These results were presented, in part, at the following meetings and symposia: 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997 (Hayes, M. J.; Lash, T. D. Abstracts of Papers; American Chemical Society: Washington, DC, 1997;ORGN 297); 30th Great Lakes Regional Meeting of the American Chemical Society, Loyola University, Chicago IL, May 1997 (Hayes, M. J.; Lash, T. D. Program and Abstracts; American Chemical Scoiety: Washington, DC, 1997; Abstract No. 128); Symposium on Theoretically Interesting Molecules, 81st Canadian Society for Chemistry Conference, Whistler, British Columbia, Canada, June 1, 1998 (Lash, T. D. Program and Abstract Book; Canadian Society for Chemistry, 1998; Abstract No. 41); 216th National Meeting of the American Chemical Society, Boston, MA, August 1998 (Spence, J. D.; Hayes, M. J.; Lash, T. D. Book of Abstracts; American CHemical Society: Washington, DC, 1998; ORGN 728); Symposium on Novel Porphyrinoids and their Metal Complexes-Chemistry, Photophysical Properties and Biomedical Aspects, 37th IUPAC Congress/27th Gesellschaft Deutscher Chemiker General Meeting, Berlin, Germany, August 1999 (Book of Abstracts, Part 1; p 174, Abstract No. MP-2219th); First International Conference on Porphyrins and Phthalocyanines (ICPP-1), Dijon, France, June 2000 (Spence, J. D.; Lash, T. D. Book of Abstracts; POST 572); 221st National Meeting of the American Chemical Society, San Diego, CA, April 2001 (Muckey, M. A.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 2001; ORGN 715).
37. These results were presented, in part, at the following meetings and symposia: 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997 (Hayes, M. J.; Lash, T. D. Abstracts of Papers; American Chemical Society: Washington, DC, 1997;ORGN 297); 30th Great Lakes Regional Meeting of the American Chemical Society, Loyola University, Chicago IL, May 1997 (Hayes, M. J.; Lash, T. D. Program and Abstracts; American Chemical Scoiety: Washington, DC, 1997; Abstract No. 128); Symposium on Theoretically Interesting Molecules, 81st Canadian Society for Chemistry Conference, Whistler, British Columbia, Canada, June 1, 1998 (Lash, T. D. Program and Abstract Book; Canadian Society for Chemistry, 1998; Abstract No. 41); 216th National Meeting of the American Chemical Society, Boston, MA, August 1998 (Spence, J. D.; Hayes, M. J.; Lash, T. D. Book of Abstracts; American CHemical Society: Washington, DC, 1998; ORGN 728); Symposium on Novel Porphyrinoids and their Metal Complexes-Chemistry, Photophysical Properties and Biomedical Aspects, 37th IUPAC Congress/27th Gesellschaft Deutscher Chemiker General Meeting, Berlin, Germany, August 1999 (Book of Abstracts, Part 1; p 174, Abstract No. MP-2219th); First International Conference on Porphyrins and Phthalocyanines (ICPP-1), Dijon, France, June 2000 (Spence, J. D.; Lash, T. D. Book of Abstracts; POST 572); 221st National Meeting of the American Chemical Society, San Diego, CA, April 2001 (Muckey, M. A.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 2001; ORGN 715).
38. These results were presented, in part, at the following meetings and symposia: 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997 (Hayes, M. J.; Lash, T. D. Abstracts of Papers; American Chemical Society: Washington, DC, 1997;ORGN 297); 30th Great Lakes Regional Meeting of the American Chemical Society, Loyola University, Chicago IL, May 1997 (Hayes, M. J.; Lash, T. D. Program and Abstracts; American Chemical Scoiety: Washington, DC, 1997; Abstract No. 128); Symposium on Theoretically Interesting Molecules, 81st Canadian Society for Chemistry Conference, Whistler, British Columbia, Canada, June 1, 1998 (Lash, T. D. Program and Abstract Book; Canadian Society for Chemistry, 1998; Abstract No. 41); 216th National Meeting of the American Chemical Society, Boston, MA, August 1998 (Spence, J. D.; Hayes, M. J.; Lash, T. D. Book of Abstracts; American CHemical Society: Washington, DC, 1998; ORGN 728); Symposium on Novel Porphyrinoids and their Metal Complexes-Chemistry, Photophysical Properties and Biomedical Aspects, 37th IUPAC Congress/27th Gesellschaft Deutscher Chemiker General Meeting, Berlin, Germany, August 1999 (Book of Abstracts, Part 1; p 174, Abstract No. MP-2219th); First International Conference on Porphyrins and Phthalocyanines (ICPP-1), Dijon, France, June 2000 (Spence, J. D.; Lash, T. D. Book of Abstracts; POST 572); 221st National Meeting of the American Chemical Society, San Diego, CA, April 2001 (Muckey, M. A.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 2001; ORGN 715).
39. These results were presented, in part, at the following meetings and symposia: 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997 (Hayes, M. J.; Lash, T. D. Abstracts of Papers; American Chemical Society: Washington, DC, 1997;ORGN 297); 30th Great Lakes Regional Meeting of the American Chemical Society, Loyola University, Chicago IL, May 1997 (Hayes, M. J.; Lash, T. D. Program and Abstracts; American Chemical Scoiety: Washington, DC, 1997; Abstract No. 128); Symposium on Theoretically Interesting Molecules, 81st Canadian Society for Chemistry Conference, Whistler, British Columbia, Canada, June 1, 1998 (Lash, T. D. Program and Abstract Book; Canadian Society for Chemistry, 1998; Abstract No. 41); 216th National Meeting of the American Chemical Society, Boston, MA, August 1998 (Spence, J. D.; Hayes, M. J.; Lash, T. D. Book of Abstracts; American CHemical Society: Washington, DC, 1998; ORGN 728); Symposium on Novel Porphyrinoids and their Metal Complexes-Chemistry, Photophysical Properties and Biomedical Aspects, 37th IUPAC Congress/27th Gesellschaft Deutscher Chemiker General Meeting, Berlin, Germany, August 1999 (Book of Abstracts, Part 1; p 174, Abstract No. MP-2219th); First International Conference on Porphyrins and Phthalocyanines (ICPP-1), Dijon, France, June 2000 (Spence, J. D.; Lash, T. D. Book of Abstracts; POST 572); 221st National Meeting of the American Chemical Society, San Diego, CA, April 2001 (Muckey, M. A.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 2001; ORGN 715).
40. These results were presented, in part, at the following meetings and symposia: 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997 (Hayes, M. J.; Lash, T. D. Abstracts of Papers; American Chemical Society: Washington, DC, 1997;ORGN 297); 30th Great Lakes Regional Meeting of the American Chemical Society, Loyola University, Chicago IL, May 1997 (Hayes, M. J.; Lash, T. D. Program and Abstracts; American Chemical Scoiety: Washington, DC, 1997; Abstract No. 128); Symposium on Theoretically Interesting Molecules, 81st Canadian Society for Chemistry Conference, Whistler, British Columbia, Canada, June 1, 1998 (Lash, T. D. Program and Abstract Book; Canadian Society for Chemistry, 1998; Abstract No. 41); 216th National Meeting of the American Chemical Society, Boston, MA, August 1998 (Spence, J. D.; Hayes, M. J.; Lash, T. D. Book of Abstracts; American CHemical Society: Washington, DC, 1998; ORGN 728); Symposium on Novel Porphyrinoids and their Metal Complexes-Chemistry, Photophysical Properties and Biomedical Aspects, 37th IUPAC Congress/27th Gesellschaft Deutscher Chemiker General Meeting, Berlin, Germany, August 1999 (Book of Abstracts, Part 1; p 174, Abstract No. MP-2219th); First International Conference on Porphyrins and Phthalocyanines (ICPP-1), Dijon, France, June 2000 (Spence, J. D.; Lash, T. D. Book of Abstracts; POST 572); 221st National Meeting of the American Chemical Society, San Diego, CA, April 2001 (Muckey, M. A.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 2001; ORGN 715).
41. These results were presented, in part, at the following meetings and symposia: 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997 (Hayes, M. J.; Lash, T. D. Abstracts of Papers; American Chemical Society: Washington, DC, 1997;ORGN 297); 30th Great Lakes Regional Meeting of the American Chemical Society, Loyola University, Chicago IL, May 1997 (Hayes, M. J.; Lash, T. D. Program and Abstracts; American Chemical Scoiety: Washington, DC, 1997; Abstract No. 128); Symposium on Theoretically Interesting Molecules, 81st Canadian Society for Chemistry Conference, Whistler, British Columbia, Canada, June 1, 1998 (Lash, T. D. Program and Abstract Book; Canadian Society for Chemistry, 1998; Abstract No. 41); 216th National Meeting of the American Chemical Society, Boston, MA, August 1998 (Spence, J. D.; Hayes, M. J.; Lash, T. D. Book of Abstracts; American CHemical Society: Washington, DC, 1998; ORGN 728); Symposium on Novel Porphyrinoids and their Metal Complexes-Chemistry, Photophysical Properties and Biomedical Aspects, 37th IUPAC Congress/27th Gesellschaft Deutscher Chemiker General Meeting, Berlin, Germany, August 1999 (Book of Abstracts, Part 1; p 174, Abstract No. MP-2219th); First International Conference on Porphyrins and Phthalocyanines (ICPP-1), Dijon, France, June 2000 (Spence, J. D.; Lash, T. D. Book of Abstracts; POST 572); 221st National Meeting of the American Chemical Society, San Diego, CA, April 2001 (Muckey, M. A.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 2001; ORGN 715).
42. These results were presented, in part, at the following meetings and symposia: 213th National Meeting of the American Chemical Society, San Francisco, CA, April 1997 (Hayes, M. J.; Lash, T. D. Abstracts of Papers; American Chemical Society: Washington, DC, 1997;ORGN 297); 30th Great Lakes Regional Meeting of the American Chemical Society, Loyola University, Chicago IL, May 1997 (Hayes, M. J.; Lash, T. D. Program and Abstracts; American Chemical Scoiety: Washington, DC, 1997; Abstract No. 128); Symposium on Theoretically Interesting Molecules, 81st Canadian Society for Chemistry Conference, Whistler, British Columbia, Canada, June 1, 1998 (Lash, T. D. Program and Abstract Book; Canadian Society for Chemistry, 1998; Abstract No. 41); 216th National Meeting of the American Chemical Society, Boston, MA, August 1998 (Spence, J. D.; Hayes, M. J.; Lash, T. D. Book of Abstracts; American CHemical Society: Washington, DC, 1998; ORGN 728); Symposium on Novel Porphyrinoids and their Metal Complexes-Chemistry, Photophysical Properties and Biomedical Aspects, 37th IUPAC Congress/27th Gesellschaft Deutscher Chemiker General Meeting, Berlin, Germany, August 1999 (Book of Abstracts, Part 1; p 174, Abstract No. MP-2219th); First International Conference on Porphyrins and Phthalocyanines (ICPP-1), Dijon, France, June 2000 (Spence, J. D.; Lash, T. D. Book of Abstracts; POST 572); 221st National Meeting of the American Chemical Society, San Diego, CA, April 2001 (Muckey, M. A.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 2001; ORGN 715).
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