engleski

Photochemistry of 5,5'-Dimethyl-2,2'-(o-phenylenedivinylene)dipyrrole

In our previous papers we demonstrated the first example of the synthesis of the bicyclo[3.2.1]octadiene derivatives by an intramolecular cycloaddition of furanic stilbene-like compounds. Contrary to the furan derivatives the styryl pyrrole 1 gives intermolecular addition product 2 in a regiospecific way. By irradiation of dipyrrole derivative 3 in benzene a ring closure to the substituted indanes followed by nucleophilic attack of the starting compound occurs giving products 4 and 5. In order to prevent dimerisation process dipyrrole derivative is substituted in the position 5 of the pyrrole ring. By irradiation of 6 bicyclo[3.2.1]octadiene derivative 7 and indane derivative 8 were obtained. The mechanism of the reaction as well as the structure determination of the products will be discussed.

photochemistry; pyrroles; intramolecular photocycloaddition

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