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Compounds with reduced porphin pi systems synthesis of 12 13 17 18 tetranorporphin the parent compound of the isobacteriochlorins



Compounds with reduced porphin pi systems synthesis of 12 13 17 18 tetranorporphin the parent compound of the isobacteriochlorins



Liebigs Annalen der Chemie (5): 1004-1011



For a comparison of the properties of porphin and isobacteriophin (4a), a synthesis of 4a via the macrocyclic diamine 3a was elaborated. The Cu complex 3b can be dehydrogenated with platinum oxide in refluxing toluene to give 4b. Using the same reaction conditions, isobacteriophin (4a) and its Pt complex 4c were obtained only in very poor yields. 4a, however, is accressible in 2% yield by flash vacuum-thermodehydrogenation of 3a. The UV spectrum of 4a is similar to spectra of isobacteriochlorin derivatives. From comparison of the 1H NMR spectra of 4a and octaethylisobacteriochlorin and enhanced planarity of the conjugated system may be deduced as a consequence of the removal of the ethanol bridges.

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Accession: 005024219

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