On the reactivity of N-tert-butyl-1,2-diaminoethane: Synthesis of 1-tert-butyl-2-imidazoline, formation of an intramolecular carbamate salt from the reaction with CO2 and generation of a hydroxyalkyl-substituted imidazolinium salt

Kieren J. Evans, Ben Potrykus, Stephen M. Mansell

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Abstract

N-tert-Butyl-1,2-diaminoethane was shown to react rapidly with atmospheric carbon dioxide to generate the zwitterionic ammonium carbamate salt CO2N(H)C2H4N(H)2tBu (1). Reaction of N-tertbutyl-1,2-diaminoethane with triethylorthoformate gave 1-tert-butyl-2-imidazoline (2) in 24% yield after fractional distillation, and the hydroxyalkyl-tethered imidazolinium salt [HOC(Me)2CH2NC2H4N(CH)tBu][Cl] (3) was synthesised from the sequential reaction of N-tert-butyl1,2-diaminoethane with isobutylene epoxide, HCl and triethylorthoformate.
Original languageEnglish
Article number1094173
Number of pages6
JournalHeteroatom Chemistry
Volume2019
DOIs
Publication statusPublished - 5 Feb 2019

ASJC Scopus subject areas

  • Chemistry(all)

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