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Photodimerisation of enones in a clay microenvironment

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Abstract

The photodimerisation of 2-cyclohexenone, 2-cyclopentenone and their 3-methyl derivatives is studied in the confined environment of clay interlayers. In the photolysis of 2-cyclohexenone, a remarkable regioselectivity is observed in favour of the head-to-head dimer when carried out in cation-exchanged bentonite clays while the dimerisation of 2-cyclopentenone favours the formation of the head-to-tail dimer. The results are explained on the basis of the ground state pre-organisation of enones and also the complexing ability of charge-balancing cations with the carbonyl oxygen of enone. In addition to the observed regioselectivity, other advantages of employing clays in photochemical studies are highlighted.

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  1. School of Chemistry, Madurai Kamaraj University, Madurai, 625 021, India

    Durairajan Madhavan & Kasi Pitchumani

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  1. Durairajan Madhavan
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  2. Kasi Pitchumani
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Correspondence to Kasi Pitchumani.

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Madhavan, D., Pitchumani, K. Photodimerisation of enones in a clay microenvironment. Photochem Photobiol Sci 1, 991–995 (2002). https://doi.org/10.1039/b208030c

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