Abstract
The potato cyst nematode is responsible for major losses in potato cultivation. In order to decrease
their presence in the soil they can be prematurely awoken using their major hatching agent:
Solanoeclepin A. This hatching agent with a structure containing multiple stereocenters and rings
varying in size from three- to seven-membered is an interesting synthetic target. This study focuses
on an intramolecular 2+2 photocycloaddition reaction in order to simultaneously form a four- and a
five-membered ring by a biradical reaction between an enone and an alkene moiety within the same
substrate. The unsaturated carbon-carbon bond of the enone is contained within a six-membered
ring, resulting in the formation of a strained tricyclic compound upon irradiation with a proficient
light source. This study aims to compare the use of light with a wavelength of 366 nm to previous
studies performed using higher energy, 300 nm irradiation for this reaction. Considering the four
substrates that were used, an overall increase in yield was realised, indicating that the lower amount
of energy input is sufficient for forming the required triplet excited enone biradical species. More
importantly, these results indicate the formation of less by-products, which are most likely caused
by an excessive energy input.