Photochemistry of the carbon–nitrogen double bond. Part 2. An investigation of the 3-methylenepropan-1-imine and 3-oxopropan-1-imine chromophores

Abstract

The synthesis of the non-conjugated imino compounds N-methoxy-2,2,4-timethyl-1-phenylpent-3-en-1-imine (8), N-methoxy-2,2-dimethyl-4,4-diphenylbut-3-en-1-imine (9), 2-(1,1-dimethyl-3,3diphenylprop-2-enyl)-4,4-dimethyl-4,5-dihydro-oxazole (10), and 2-benzoyl-N-methoxy-2-methylpropan-1-imine (11) is described and their photochemistry reported. cis-trans Isomerisation was observed for compounds (8) and (11), the latter also undergoing N–O bond fission to yield 2-benzoyl-2-methylpropiononitrile (35). Compound (9) formed photoproducts in only trace amounts whereas the dihydro-oxazole (10) was photochemically inert.