engleski

Synthesis and photochemistry of styryl substituted annelated furan derivatives

New substituted benzo- and naphthofuryl derivatives (5, 6, 7) of o-divinylbenzene, were synthesized and irradiated in order to form annelated bicyclo[3.2.1]octadienes. While 2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan (5) upon irradiation gives the bicyclo[3.2.1]octadiene derivative (12) in 65 yield, 2-[2-(2-vinylphenyl)ethenyl]naphtho[2, 1-b]furan (6) and 2-[2-(2-vinylphenyl)ethenyl]naphtho[1, 2-b]furan (7), undergo cis-trans isomerizationbut not form intramolecular photocycloaddition products. The mechanism of the intramolecular [2+2] photocycloaddition is explained via intermediate (17) which was proved by the formation of products (18) and (19), by irradiation in methanol and deuteromethanol.

photochemistry ; synthesis of annelated furans ; cis-trans-isomerization ; benzofuran ; naphthofuran

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