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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

Evans, Kieren J., Potrykus, Ben and Mansell, Stephen M. 2019. 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. Heteroatom Chemistry 2019 , 1094173. 10.1155/2019/1094173

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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)C2H4NBu (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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Cardiff Catalysis Institute (CCI)
Publisher: Hindawi
ISSN: 1042-7163
Date of First Compliant Deposit: 17 November 2021
Date of Acceptance: 14 January 2019
Last Modified: 23 Nov 2021 19:10
URI: https://orca.cardiff.ac.uk/id/eprint/145503

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