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.
Highlights
1,2-Diamines, exemplified by ethylenediamine and its derivatives, are produced on a large scale and are used for many purposes including coordination chemistry [1] and CO2 capture [2,3,4,5,6]
N-substituted ethylenediamines can function as precursors to 1-substituted-2-imidazolines [10, 11], with the synthesis of unsymmetrical saturated N-heterocyclic carbenes (NHCs) one potential application for these compounds [12, 13]
Examples of 2-imidazolines that are widely used in the synthesis of unsymmetrical saturated NHCs include those with mesityl (2,4,6-Me3C6H2) and 2,6-diisopropylphenyl (Dipp: 2,6-iPr2C6H3) substituents [12, 13]. 1-Ethyl-2-imidazoline and 1-benzyl-2-imidazoline are known compounds [14], but the tert-butyl derivative, to the best of our knowledge, has not been reported
Summary
1,2-Diamines, exemplified by ethylenediamine and its derivatives, are produced on a large scale and are used for many purposes including coordination chemistry [1] and CO2 capture [2,3,4,5,6]. N-substituted ethylenediamines can function as precursors to 1-substituted-2-imidazolines (dihydroimidazoles) [10, 11], with the synthesis of unsymmetrical saturated N-heterocyclic carbenes (NHCs) one potential application for these compounds [12, 13]. Examples of 2-imidazolines that are widely used in the synthesis of unsymmetrical saturated NHCs include those with mesityl (2,4,6-Me3C6H2) and 2,6-diisopropylphenyl (Dipp: 2,6-iPr2C6H3) substituents [12, 13]. 1-Ethyl-2-imidazoline and 1-benzyl-2-imidazoline are known compounds [14], but the tert-butyl derivative, to the best of our knowledge, has not been reported. N-substituted-1,2-diaminoethanes to form fluorenyl tethered diamines [21], which acted as useful precursors to a tethered N-heterocyclic stannylene (NHSn) with a Dipp substituent [21]. We characterise the reaction product of N-tert-butyl-1,2-diaminoethane with carbon dioxide, the synthesis of 1-tert-butyl-2-imidazoline, and the formation of a hydroxyalkyl imidazolinium salt with an N-tert-butyl substituent
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