Heterocyclic polyfluoro-compounds. Part 25. The photochemical addition of ethylene to pentafluoropyridine: formation of 1 : 1- and 2 : 1-adducts
Abstract
Ethylene adds photochemically to pentafluoropyridine to yield 1,2,4,5,6-pentafluoro-3-azabicyclo[4.2.0]octa-2,4-diene (1) and 1,2,5,6,8-pentafluoro-7-azatricyclo[4.2.2.02.5]dec-7-ene (2). The adduct (2) is also slowly formed thermally from (1). Water converts the CF:N group in adduct (2) into CO·NH, and ethanol converts it into C(OEt):N. Lithium aluminium hydride effects complete reduction and replacement of fluorine atoms by hydrogen.