10.1021/jo00234a002
The research investigates the photochemical and thermal transformations of several 2(3H)-furanones, including 3-benzyl-3,5-diphenyl-2(3H)-furanone (la), 3-benzyl-3-(4-methylphenyl)-5-phenyl-2(3H)-furanone (lb), 3-benzyl-3-(4-methoxyphenyl)-5-phenyl-2(3H)-furanone (IC), 3,3-dibenzyl-5-phenyl-2(3H)-furanone (Id), 3-benzyl-3-phenylphenanthro[9,10-b]furan-2(3H)-one (le), and 3-benzoyl-3,5-diphenyl-2(3H)-furanone (If). The purpose is to understand the reaction pathways and mechanisms under different conditions. The study found that under direct irradiation, these furanones undergo decarbonylation and bond cleavage at the benzyl or benzoyl group, leading to various products such as furans, butenones, and rearranged lactones. For example, the photolysis of la in benzene or methanol produced 2,3,5-triphenylfuran (3a) and 1,3,5-triphenylbut-3-en-l-one (6a), while sensitized irradiation with acetophenone yielded the rearranged lactone 9a and bis lactone 10a. The thermal transformations of la-d led to the formation of 2(5H)-furanones 9a-d. Laser flash photolysis studies revealed that the triplets of these furanones have short lifetimes and undergo bond cleavage to form furanoxy radicals. The study concludes that the photochemical and thermal transformations of these furanones are influenced by the substituents and the excitation conditions, with singlet-mediated decarbonylation, triplet-sensitized bond cleavage, and [1,3]-sigmatropic shifts being the key mechanisms.