Direct Routes to 5,15-Diaryl-10,20-Diethynyl Porphyrins from Pyrrole

Synlett

Volumn 1996, Issue 11, 1996, Pages 1039-1040

  Wilson, G Scott ^a   Anderson, Harry L ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002699267     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5679     Document Type: Article

References (29)

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23. We are grateful to Dr D. W. J. McCallien for preparing 4b according to the method of M. S. Newman, L. F. Lee, J. Org. Chem. 1972, 37, 4468.
24. We are grateful to Dr P. L. Burn and R. Beavington for discussing with us their unpublished work on the synthesis of 2b.
25. J. S. Lindsey, R. W. Wagner, J. Org. Chem. 1989, 54, 828; J. S. Lindey, I. C. Schreiman, H. C. Hsu, P. C. Kearney, A. M. Marguerettaz, J. Org. Chem. 1987, 52, 827.
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27. Triisopropylsilylpropynal was prepared from triisopropylsilylethyne in 94% yield by treatment with butyl lithium followed by dimethyl formamide, by analogy with the published procedure for trimethylsilylpropynal; K. J. H. Kruithof, R. F. Schmitz, G. W. Klumpp, Tetrahedron 1983, 39, 3073.
28. While this communication was in preparation a related synthesis of porphyrins from meso-(arylethynyl)dipyrromethanes was reported by L. R. Milgrom, G. Yahioglu, Tetrahedron Lett. 1996, 37, 4069.
29. 13C NMR resonances are broad and the α-pyrrolic resonances are too broad to reliably identify due to intermediate rate tautomerism at room temperature.