The photochemistry of citral

Citral (I) is cyclized by UV irradiation1 to 2-isopropenyl-5-methylcyclopentane-carboxaldehyde (II), containing the carbon skeleton of the monoterpenes of ants and catmint. 1,6,6-Trimethylbicyclo[2,1,1]hexane-2α-carboxaldehyde (XII, R = H), produced in lesser amount at the same time, was synthesized from camphor. The two photocitrals may, perhaps, come from a common intermediate containing the cyclopentane ring.