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
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 fraction...
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| Format: | Article |
| Language: | English |
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Wiley
2019-01-01
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| Series: | Heteroatom Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2019/1094173 |
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| author | Kieren J. Evans Ben Potrykus Stephen M. Mansell |
| author_facet | Kieren J. Evans Ben Potrykus Stephen M. Mansell |
| author_sort | Kieren J. Evans |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-ba0f3e018005412a8fa8fbdde7d09b85 |
| institution | Kabale University |
| issn | 1042-7163 1098-1071 |
| language | English |
| publishDate | 2019-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Heteroatom Chemistry |
| spelling | doaj-art-ba0f3e018005412a8fa8fbdde7d09b852025-02-03T05:48:27ZengWileyHeteroatom Chemistry1042-71631098-10712019-01-01201910.1155/2019/10941731094173On 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 SaltKieren J. Evans0Ben Potrykus1Stephen M. Mansell2Institute of Chemical Sciences, School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UKInstitute of Chemical Sciences, School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UKInstitute of Chemical Sciences, School of Engineering and Physical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UKN-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.http://dx.doi.org/10.1155/2019/1094173 |
| spellingShingle | Kieren J. Evans Ben Potrykus Stephen M. Mansell 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 |
| 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| url | http://dx.doi.org/10.1155/2019/1094173 |
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