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

doi:10.1155/2019/1094173

Paper

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

Published Feb 5, 2019 · Kieren J. Evans, B. Potrykus, S. M. Mansell

Heteroatom Chemistry

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3

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0

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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-tert-butyl-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-butyl-1,2-diaminoethane with isobutylene epoxide, HCl, and triethylorthoformate.

Study Snapshot

N-tert-butyl-1,2-diaminoethane rapidly reacts with atmospheric carbon dioxide to produce a zwitterionic ammonium carbamate salt, and hydroxyalkyl-substituted imidazolinium salt.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

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

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References

Citations

Cooperative catalysis of Ru(III)-porphyrin in CO2-involved synthesis of oxazolidinones.

The Ru(III)-porphyrin catalyst efficiently catalyzes the CO2-induced synthesis of oxazolidinones, yielding 71-91% of the product in 71-91% of the reaction time.

Recent Advances in the Synthesis of Imidazolines (2009–2020)

Recent advances in the synthesis of imidazoline scaffolds have significantly improved the production of natural and pharmaceutical products.

Syntheses of Bis(N-heterocyclic carbene)s and their application in main-group chemistry

Bis(N-heterocyclic carbene)s show potential in stabilizing main-group elements in unusual oxidation states and enabling novel compound synthesis, but their potential for main-group elements remains unrealized.