Abstract
The photochemical irradiation of acrylonitrile derivatives bearing either aromatic or heteroaromatic rings as substituents on C-3 gives dimeric products. The reactions were carried out in acetonitrile in the presence of benzophenone as sensitizer. The most abundant dimer showed a structure similar to dimeric compounds isolated in Caribbean sponges showing antimicrobial activity. The regiochemical control in the formation of the dimers can be rationalised considering the overlap of the frontier orbitals involved in the reaction. The stereochemistry can be explained considering the heat of formation of the dimers: the most stable dimers are formed.
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