A. Yasuhara, S. Akiyama, M. Nakagawa
Dec 1, 1972
Citations
0
Influential Citations
13
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
Syntheses of di-1-naphthyl- and di-2-naphthylpolyenes (In, n=1–4,6 and In′, n=1–6) have been carried out by the Wittig reaction. Naphthaldehydes (III and III′), 3-naphthyl-2-propenals (V and V′), 5-naphthyl-2,4-pentadienals (VI and VI′) and muconic aldehyde were used as carbonyl components. Naphthylmethyltriphenylphosphonium halides (IV and IV′), 3-naphthyl-2-propenyltriphenylphosphonium bromides (XI and XI′) and 5-(2-naphthyl)-2,4-pentadienyltriphenylphosphonium bromide (XII′) were synthesized and converted into the corresponding phosphoranes by reaction with phenyllithium. The reaction of carbonyl moiety with phosphorane by a proper combination afforded dinaphthylpolyenes (In and In′). The electronic spectra of di-1-naphthylpolyenes (In) showed broad and structureless absorption curves. In contrast, the absorption curves of di-2-naphthylpolyenes (In′) exhibited a distinct vibrational fine structure. It was found that the bathochromic shift of the longest-wavelength peak (λmax) along with the increase of...