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

doi:10.1155/2019/1094173

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

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

63 Downloads (Pure)

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)₂^tBu (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 language	English
Article number	1094173
Number of pages	6
Journal	Heteroatom Chemistry
Volume	2019
DOIs	https://doi.org/10.1155/2019/1094173
Publication status	Published - 5 Feb 2019

ASJC Scopus subject areas

General Chemistry

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@article{8e078c8bc159413b99b0bee4ebb70d8c,

title = "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",

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.",

author = "Evans, \{Kieren J.\} and Ben Potrykus and Mansell, \{Stephen M.\}",

year = "2019",

month = feb,

day = "5",

doi = "10.1155/2019/1094173",

language = "English",

volume = "2019",

journal = "Heteroatom Chemistry",

issn = "1042-7163",

publisher = "John Wiley and Sons Inc",

}

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; Mansell, Stephen M.
In: Heteroatom Chemistry, Vol. 2019, 1094173, 05.02.2019.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - 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

AU - Evans, Kieren J.

AU - Potrykus, Ben

AU - Mansell, Stephen M.

PY - 2019/2/5

Y1 - 2019/2/5

N2 - 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.

AB - 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.

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U2 - 10.1155/2019/1094173

DO - 10.1155/2019/1094173

M3 - Article

SN - 1042-7163

VL - 2019

JO - Heteroatom Chemistry

JF - Heteroatom Chemistry

M1 - 1094173

ER -