5-Aryl-1,9-dichlorodipyrrins react with a series of S- and N- nucleophiles (both alkyl- and aryl- ones). Reagents with mercapto group yield product of double nucleophilic substitution of 5-pheny-1,9-dichlorodipyrrin, i.e. the respective 1,9-bis(alkyl-of arylthio)dipyrrin. On the contrary, 5-(4-nitrophenyl)-1,9-dichlorodipyrrin causes disulfides formation from the S-aliphatic substrates, whereas nucleophilic substitution remains the main path of the reaction for S-aryl ones. The reaction of N-Alkyl nucleophiles proceeds as mono-substitution. UV-Vis spectra feature a batochromic shift for bis-S-substituted products and a hypsochromic shift for mono-N-substituted ones, with respect to the starting dichlrorides.
- Nucleophilic substitution
- UV-Vis spectra