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Volumn 69, Issue 25, 2004, Pages 8842-8850

Synthesis of sapphyrins, heterosapphyrins, and carbasapphyrins by a "4 + 1" approach

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CONDENSATION REACTIONS; ORGANIC ACIDS; PORPHYRINS;

EID: 10044247395     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040239o     Document Type: Article
Times cited : (70)

References (96)
  • 1
    • 0001096123 scopus 로고
    • Smith, K. M., Ed.; Elsevier: Amsterdam, The Netherlands
    • Johnson, A. W. In Porphyrins and Metalloporphyrins; Smith, K. M., Ed.; Elsevier: Amsterdam, The Netherlands, 1975; pp 729-754.
    • (1975) Porphyrins and Metalloporphyrins , pp. 729-754
    • Johnson, A.W.1
  • 4
    • 0002484311 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA
    • Sessler, J. L.; Gebauer, A.; Weghorn, S. J. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 2, pp 55-124.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 55-124
    • Sessler, J.L.1    Gebauer, A.2    Weghorn, S.J.3
  • 12
    • 10044287937 scopus 로고    scopus 로고
    • note
    • Woodward's announcement on the synthesis of the sapphyrin system at the 1966 Aromaticity Conference in Sheffield is consistently acknowledged in the literature10,11,15 but no mention of this accomplishment is made in the published proceedings for this meeting.
  • 16
    • 10044291458 scopus 로고    scopus 로고
    • note
    • Porphyrins are nearly always isolated as purple crystalline materials and Hoppe-Seyler coined the name hematoporphyrin for the purple substance derived by treating hemoglobin with aqueous sulfuric acid from the Greek for blood and purple: Hoppe-Seyler, F. Med.-Chem. Unters. 1871, 4, 531 and 540. Similarly, chlorin, the parent hydroporphyrin structure for the chlorophylls, takes its name from the Greek word chloris for green. Woodward proposed the term sapphyrin by analogy to the names of these "Pigments of Life" and similarly used the name smaragdyrin (from the Greek word for emerald) for the related norsapphyrins.10 The use of color-related names for expanded porphyrins was later further popularized by Sessler and other researchers in the field.3,4,6
  • 29
    • 0000303285 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA
    • (b) Pandey, R. K.; Zheng, G. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 6, pp 157-230.
    • (2000) The Porphyrin Handbook , vol.6 , pp. 157-230
    • Pandey, R.K.1    Zheng, G.2
  • 39
    • 0001004194 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA
    • Lash, T. D. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 2, pp 125-199.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 125-199
    • Lash, T.D.1
  • 42
    • 0012831123 scopus 로고
    • The "3 + 1" designation refers to the number of pyrrole rings (or surrogates) in each of the components used for these syntheses. In the work discussed here, the "3 + 1", "3 + 2", and "4 + 1" methods are all based upon the MacDonald "2 + 2" condensation where a dipyrrylmethane is condensed with a dipyrrylmethane dialdehyde: Arsenault, G. P.; Bullock, E.; MacDonald, S. F. J. Am. Chem. Soc. 1960, 82, 4384.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 4384
    • Arsenault, G.P.1    Bullock, E.2    MacDonald, S.F.3
  • 72
    • 10044292039 scopus 로고    scopus 로고
    • Illinois Wesleyan University, Bloomington, IL, October
    • These results were presented, in part, at the following meetings: 89th Annual Meeting of the Illinois State Academy of Science, Illinois Wesleyan University, Bloomington, IL, October 1996 (Richter, D. T.; Lash, T. D. Transactions of the Illinois State Academy of Science; 1996; Supplement to Vol. 89, p 55, Abstract No. 47); 213th National ACS Meeting, San Francisco, CA, April 1997 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1997; CHED 439); 31st Great Lakes Regional ACS Meeting, University of Wisconsin-Milwaukee, June 1998 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 190); 216th National ACS Meeting, Boston, MA, August 1998 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1998; ORGN 593); 31st Central Regional ACS Meeting, Ohio State University, Columbus, OH, June 1999 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 265).
    • (1996) 89th Annual Meeting of the Illinois State Academy of Science
  • 73
    • 10044267284 scopus 로고    scopus 로고
    • Abstract No. 47
    • These results were presented, in part, at the following meetings: 89th Annual Meeting of the Illinois State Academy of Science, Illinois Wesleyan University, Bloomington, IL, October 1996 (Richter, D. T.; Lash, T. D. Transactions of the Illinois State Academy of Science; 1996; Supplement to Vol. 89, p 55, Abstract No. 47); 213th National ACS Meeting, San Francisco, CA, April 1997 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1997; CHED 439); 31st Great Lakes Regional ACS Meeting, University of Wisconsin-Milwaukee, June 1998 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 190); 216th National ACS Meeting, Boston, MA, August 1998 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1998; ORGN 593); 31st Central Regional ACS Meeting, Ohio State University, Columbus, OH, June 1999 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 265).
    • (1996) Transactions of the Illinois State Academy of Science , Issue.SUPPL. TO VOL. 89 , pp. 55
    • Richter, D.T.1    Lash, T.D.2
  • 74
    • 0010460437 scopus 로고    scopus 로고
    • San Francisco, CA, April
    • These results were presented, in part, at the following meetings: 89th Annual Meeting of the Illinois State Academy of Science, Illinois Wesleyan University, Bloomington, IL, October 1996 (Richter, D. T.; Lash, T. D. Transactions of the Illinois State Academy of Science; 1996; Supplement to Vol. 89, p 55, Abstract No. 47); 213th National ACS Meeting, San Francisco, CA, April 1997 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1997; CHED 439); 31st Great Lakes Regional ACS Meeting, University of Wisconsin-Milwaukee, June 1998 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 190); 216th National ACS Meeting, Boston, MA, August 1998 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1998; ORGN 593); 31st Central Regional ACS Meeting, Ohio State University, Columbus, OH, June 1999 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 265).
    • (1997) 213th National ACS Meeting
  • 75
    • 10044291457 scopus 로고    scopus 로고
    • American Chemical Society: Washington, DC; CHED 439
    • These results were presented, in part, at the following meetings: 89th Annual Meeting of the Illinois State Academy of Science, Illinois Wesleyan University, Bloomington, IL, October 1996 (Richter, D. T.; Lash, T. D. Transactions of the Illinois State Academy of Science; 1996; Supplement to Vol. 89, p 55, Abstract No. 47); 213th National ACS Meeting, San Francisco, CA, April 1997 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1997; CHED 439); 31st Great Lakes Regional ACS Meeting, University of Wisconsin-Milwaukee, June 1998 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 190); 216th National ACS Meeting, Boston, MA, August 1998 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1998; ORGN 593); 31st Central Regional ACS Meeting, Ohio State University, Columbus, OH, June 1999 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 265).
    • (1997) Book of Abstracts
    • Richter, D.T.1    Lash, T.D.2
  • 76
    • 10044277644 scopus 로고    scopus 로고
    • University of Wisconsin-Milwaukee, June (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 190)
    • These results were presented, in part, at the following meetings: 89th Annual Meeting of the Illinois State Academy of Science, Illinois Wesleyan University, Bloomington, IL, October 1996 (Richter, D. T.; Lash, T. D. Transactions of the Illinois State Academy of Science; 1996; Supplement to Vol. 89, p 55, Abstract No. 47); 213th National ACS Meeting, San Francisco, CA, April 1997 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1997; CHED 439); 31st Great Lakes Regional ACS Meeting, University of Wisconsin-Milwaukee, June 1998 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 190); 216th National ACS Meeting, Boston, MA, August 1998 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1998; ORGN 593); 31st Central Regional ACS Meeting, Ohio State University, Columbus, OH, June 1999 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 265).
    • (1998) 31st Great Lakes Regional ACS Meeting
  • 77
    • 0004323191 scopus 로고    scopus 로고
    • Boston, MA, August
    • These results were presented, in part, at the following meetings: 89th Annual Meeting of the Illinois State Academy of Science, Illinois Wesleyan University, Bloomington, IL, October 1996 (Richter, D. T.; Lash, T. D. Transactions of the Illinois State Academy of Science; 1996; Supplement to Vol. 89, p 55, Abstract No. 47); 213th National ACS Meeting, San Francisco, CA, April 1997 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1997; CHED 439); 31st Great Lakes Regional ACS Meeting, University of Wisconsin-Milwaukee, June 1998 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 190); 216th National ACS Meeting, Boston, MA, August 1998 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1998; ORGN 593); 31st Central Regional ACS Meeting, Ohio State University, Columbus, OH, June 1999 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 265).
    • (1998) 216th National ACS Meeting
  • 78
    • 10044291457 scopus 로고    scopus 로고
    • American Chemical Society: Washington, DC; ORGN 593)
    • These results were presented, in part, at the following meetings: 89th Annual Meeting of the Illinois State Academy of Science, Illinois Wesleyan University, Bloomington, IL, October 1996 (Richter, D. T.; Lash, T. D. Transactions of the Illinois State Academy of Science; 1996; Supplement to Vol. 89, p 55, Abstract No. 47); 213th National ACS Meeting, San Francisco, CA, April 1997 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1997; CHED 439); 31st Great Lakes Regional ACS Meeting, University of Wisconsin-Milwaukee, June 1998 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 190); 216th National ACS Meeting, Boston, MA, August 1998 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1998; ORGN 593); 31st Central Regional ACS Meeting, Ohio State University, Columbus, OH, June 1999 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 265).
    • (1998) Book of Abstracts
    • Richter, D.T.1    Lash, T.D.2
  • 79
    • 10044271658 scopus 로고    scopus 로고
    • Ohio State University, Columbus, OH, June
    • These results were presented, in part, at the following meetings: 89th Annual Meeting of the Illinois State Academy of Science, Illinois Wesleyan University, Bloomington, IL, October 1996 (Richter, D. T.; Lash, T. D. Transactions of the Illinois State Academy of Science; 1996; Supplement to Vol. 89, p 55, Abstract No. 47); 213th National ACS Meeting, San Francisco, CA, April 1997 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1997; CHED 439); 31st Great Lakes Regional ACS Meeting, University of Wisconsin-Milwaukee, June 1998 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 190); 216th National ACS Meeting, Boston, MA, August 1998 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1998; ORGN 593); 31st Central Regional ACS Meeting, Ohio State University, Columbus, OH, June 1999 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 265).
    • (1999) 31st Central Regional ACS Meeting
  • 80
    • 10044227974 scopus 로고    scopus 로고
    • Abstract No. 265
    • These results were presented, in part, at the following meetings: 89th Annual Meeting of the Illinois State Academy of Science, Illinois Wesleyan University, Bloomington, IL, October 1996 (Richter, D. T.; Lash, T. D. Transactions of the Illinois State Academy of Science; 1996; Supplement to Vol. 89, p 55, Abstract No. 47); 213th National ACS Meeting, San Francisco, CA, April 1997 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1997; CHED 439); 31st Great Lakes Regional ACS Meeting, University of Wisconsin-Milwaukee, June 1998 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 190); 216th National ACS Meeting, Boston, MA, August 1998 (Richter, D. T.; Lash, T. D. Book of Abstracts; American Chemical Society: Washington, DC, 1998; ORGN 593); 31st Central Regional ACS Meeting, Ohio State University, Columbus, OH, June 1999 (Richter, D. T.; Lash, T. D. Program and Abstracts; Abstract No. 265).
    • Program and Abstracts
    • Richter, D.T.1    Lash, T.D.2
  • 84
  • 85
    • 0003026147 scopus 로고    scopus 로고
    • Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA
    • Medforth, C. J. In The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000; Vol. 5, pp 1-80.
    • (2000) The Porphyrin Handbook , vol.5 , pp. 1-80
    • Medforth, C.J.1


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