Efficient synthesis of monoacyl dipyrromethanes and their use in the preparation of sterically unhindered trans-porphyrins

Journal of Organic Chemistry

Volumn 65, Issue 4, 2000, Pages 1084-1092

  Rao, Polisetti Dharma ^a   Littler, Benjamin J ^a   Geier III, G Richard ^a   Lindsey, Jonathan S ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

METHANE; PORPHYRIN;

ACYLATION; ARTICLE; CATALYSIS; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; MASS SPECTROMETRY; REACTION ANALYSIS; STEREOCHEMISTRY;

ACYLATION; MAGNETIC RESONANCE SPECTROSCOPY; METHANE; MOLECULAR STRUCTURE; PORPHYRINS; PYRROLES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 0034712301     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9915473     Document Type: Article

References (22)

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2. Lindsey, J. S. In The Porphyrin Handbook; Kadish, K. M., Smith, K., Guilard, R., Eds.; Academic Press: San Diego, CA 1999; Vol. 1, pp 45-118.
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7. Lee, C.-H.; Li, F.; Iwamoto, K.; Dadok, J.; Bothner-By, A. A.; Lindsey, J. S. Tetrahedron 1995, 51, 11645-11672.
8. Araki, M.; Sakata, S.; Takei, H.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1974, 47, 1777-1780.
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11. Rao, P. D.; Dhanalekshmi, S.; Littler, B. J.; Lindsey, J. S. Manuscript in preparation.
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13. The limit of detection of scrambled porphyrins by LD-MS is approximately 1 part in 100 (see the Experimental Section). Thus, for a trans-porphyrin yield of 25%, any putative single scrambled porphyrin (except the cis-porphyrin) would be present in no greater than 0.25% yield. Note that the MS method cannot exclude scrambling leading exclusively to the cis-porphyrin. However, rearrangement processes leading to such an isomer would be expected to form a distribution of porphyrin products, including those of other masses. See ref 3.
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17. Wagner, R. W.; Johnson, T. E.; Lindsey, J. S. J. Am. Chem. Soc. 1996, 118, 11166-11180. Lindsey, J. S. In Modular Chemistry; Michl, J., Ed.; NATO ASI Series C: Mathematical and Physical Sciences, Vol. 499; Kluwer Academic Publishers: Dordrecht, 1997; pp 517-528.
18. (a) Fenyo, D.; Chait, B. T.; Johnson, T. E.; Lindsey, J. S. J. Porphyrins Phthalocyanines 1997, 1, 93-99.
19. (b) Srinivasan, N.; Haney, C. A.; Lindsey, J. S.; Zhang, W.; Chait, B. T. J. Porphyrins Phthalocyanines 1999, 3, 283-291.
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