Synthesis of some 9-Alkenylanthracenes and its Cycloaddition: Adducts of 2-Bromoacrylaldehyde

Author(s): Adel Al-Saeedi, Usama Karama, Mohammad Mohsin and Mazahar Farooqui

Anthracene and its derivatives can behave as a diene; therefore, it has ability to undergo cycloaddition reactions with a variety of dienophiles at position 9 and 10, where the lowest benzenoid character exists. This research ai ms to synthesis some 9-alkenylanthracenes, such as 9- vinylanthracene (9-ethenylanthracne), 9-prop-2-enyl-anthracene (9-allylan thracene), 9-but-3-enyl-anthracene (9-homoallylanthracene), and 9-pent-4 -enyl-anthracene and its cycloadd ition with 2-bromoacrylaldehyde to give both possible [4+2] cycloadduct (ortho and/or meta). The results showed th at ortho is preferred in all of the experimental cases with good yields.

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