Abstract
In the photocycloaddition of benzene to alkenes, products are formed in the ortho and meta addition modes; in the photoaddition of benzene to the terminal atoms of a diene system, products are formed in the meta and para modes. On the basis of orbital symmetry correlations, meta photocycloaddition has been described as an allowed process. The situation regarding the ortho and para modes is less clear. It is shown that orbital symmetry correlations can also be used to predict the occurrence of reactive minima or funnels in the potential energy surface of the first excited state of the reactants. The presence of these funnels can be used to rationalize the abundance of ortho and meta adducts in the photoaddition of arenes to alkenes, and the occurrence of meta and para adducts in the photoaddition of arenes to dienes. The role of charge transfer in the selection of the addition mode and in the regioselectivity in the ortho mode for arenes to alkenes is discussed.
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