Abstract
Abstract The photocycloaddition of propanal to 1,3-cyclohexadiene leads to oxetanes, as well as to the dimers of 1,3-cyclohexadiene. A mechanism of oxetane formation is proposed in which singlet excited propanal attacks a ground-state 1,3-cyclohexadiene to give a singlet complex with a charge-transfer character. The complex either decays to the ground-state reactants or reacts to give oxetanes. Quantum yield measurements and kinetic analysis show a rate constant of 4×109 M−1 s−1 for singlet complex formation from propanal and 1,3-cyclohexadiene in benzene. The quenching data of propanal fluorescence support such a mechanism.
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