Abstract
Wittig reaction of 2,7-di-tert-butylpyrene-4-carbaldehyde with benzyltriphenylphosphonium salts in the presense of n-BuLi gave 2,7-di-tert-butyl-4-(phenylethenyl)pyrenes, from which naphthalene condensed aromatic compounds, 2,7-di-tert-butyl-dibenzo[ij, no]tetraphenes, were obtained by photo-induced cyclisation in the presense of iodine.
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