EFFICIENT CLEAVAGE OF CYCLOPROPYL BOND BY ADJACENT KETYL RADICAL GENERATED UNDER PET CONDITIONS

Photolysis of various conjugated cyclopropyl and epoxy ketones in 20% triethyl amine (TEA) and ethanol leads to cleavage of cyclopropyl bond . Significant wavelength dependence phenomenon is observed during phot olysis for the cleanliness and efficient photo transformation. Steroid al cyclopropyl ketones cleave efficiently at 300nm photolysis, whereas exo-cyclopropyl ketones cleave at 254 nm. The regiochemistry of cyclo propyl bond cleavage is governed by the principle of maximum overlap. The nature of chemistry generated by ketyl radical is shown to be a fu nction of methodology of their generation.