Bisnaphthohexaphyrin

Similarly, the DA reaction of o-benzoquinodimethane with the hexaphyrin 16, followed by treatment with DDQ, gave rise to the naphthohexaphyrin 17 <05AC(E)932>. This result revealed that the first addition of the diene took place selectively at the inner inverted beta-pyrrolic double bond, suggesting that this double bond is the most reactive position of the macrocycle. In minor amount the reaction also gave rise to a bisnaphthohexaphyrin. Curiously, this compound resulted from the selective addition of a second o-benzoquinodimethane species to an outer befa-pyrrolic double bond of the naphthohexaphyrin 17, and is in agreement with the theoretical calculations that predicted that the second cycloaddition could not occur at the other side of the inner double bond of 17. 

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See also in sourсe #XX -- [ ]

See also in sourсe #XX -- [ ]

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