SNAr nucleophilic substitution of 1,9-dihalodipyrrins by S- and N- nucleophiles. Synthesis of new dipyrrins bearing pendant substituents

Evgenia Leushina, Ksenia Tikhomirova, Anastasiya Permyakova, Pavel Ilin, Maria Terenina, Alexander Anisimov, Andrey Khoroshutin

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)149-155
Number of pages7
JournalDyes and Pigments
Volume129
DOIs
Publication statusPublished - 1 Jun 2016
Externally publishedYes

Keywords

  • 1,9-dihalo-H-dipyrrins
  • N-nucleophiles
  • NMR
  • Nucleophilic substitution
  • S-nucleophiles
  • UV-Vis spectra

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