Arylation of sensitive 1-(Pyrrolidin-1-yl)-diazen-1-ium-diolate in ionic liquids

Carlos A. Velázquez, Geoffrey M. Lynn, Vineet Kumar, Larry K. Keefer, Sanjay V. Malhotra

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

The purpose of this research was to investigate the stability and reactivity of 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (PYRRO/NO) in dimethylformamide (DMF, as the reference solvent) and compare them to those obtained using different ionic liquids. The results of our experiments showed that PYRRO/NO is more stable (based on reactivity) in ionic liquid [EMIM][Ms] (with reaction yields up to 52%) than in DMF, that substitution products can be separated directly and quantitatively from the ionic liquid using a single flash-column separation, and that the ionic liquids can also be recovered and reused in a second iteration of the same reaction to achieve similar yields.

Original languageEnglish (US)
Pages (from-to)1322-1332
Number of pages11
JournalSynthetic Communications
Volume40
Issue number9
DOIs
StatePublished - Jan 2010
Externally publishedYes

Keywords

  • Diazeniumdiolate
  • Ionic liquid
  • Nitric oxide donor
  • Nucleophilic displacement

ASJC Scopus subject areas

  • Organic Chemistry

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