On the Photochemistry of (Z,Z)-2,7-cyclodecadien-1-one and 4,8-Cyclododecadien-1-one. Synthesis and Properties of Tricyclo2,8>decane Systems

Article abstract of DOI:10.1002/hlca.19860690815

Irradiation of (Z,Z)-2,7-cyclodecadien-1-one (3) yelds (Z,Z)-3,7-cyclodecadien-1-one (12) or tricyclo<5.3.0.0^2,8>decan-4-one (16), depending on the reaction conditions.Irradiation of 4,8-cyclododecadien-1-one (28)results also in a light-induced transannular <2 + 2> cycloaddition, yielding tetracyclo<7.3.0.0^2.100^3,6>dodecan-1-one (30).Starting from 16, the preparation of tricyclo<5.3.0.0^2,8>decane (19), tricyclo<5.3.0.0^2,8>dec-4-ene (21) and tricyclo<5.3.0.0^2,8>deca-3,5-diene (24) is described.The 1H-NMR and 13C-NMR spectra of the newly prepared compounds are discussed.In the case of 19, 21, and 24, the electronic structure is discussed on hand of their PE spectra.