1,5-Diazacyclooctane: Difference between revisions
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==Synthesis and reactions== |
==Synthesis and reactions== |
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It is prepared in low yield by the alkylation of [[ |
It is prepared in low yield by the alkylation of [[ammonia]] with [[1,3-Dibromopropane|1,3-dibromopropane]].<ref>{{cite book|title=1,5-Diazacyclooctane, Pendant Arm Thiolato Derivatives and [N,N'-Bis(2-mercaptoethyl)-1,5-diazacyclooctanato]nickel(II)|author1=Daniel K. Mills |author2=Ivan Font |author3=Patrick J. Farmer |author4=Yui-May Hsiao |author5=Thawatchai Tuntulani |author6=Rizalia M. Buonomo |author7=Dawn C. Goodman |author8=Ghezai Musie |author9=Craig A. Grapperhaus |author10=Michael J. Maguire |author11=Chia-Huei Lai |author12=Michelle L. Hatley |author13=Jason J. Smee |author14=John A. Bellefeuille |author15=Marcetta Y. Darensbourg |display-authors=3 |series=Inorganic Syntheses|year=1998|volume=32|pages=89–98|doi=10.1002/9780470132630.ch15}}</ref> |
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The N-H centers can be replaced with many other groups. As a bis secondary amine, it condenses with [[aldehyde]]s to give bicyclic derivatives.<ref>{{cite journal|title=Reaction of 1,5-Diazacyclooctane with Aldehydes|author1=Billman, John H. |author2=Dorman, Linneaus C.|journal=Journal of Organic Chemistry|year=1962|volume=27|pages=2419–22|doi=10.1021/jo01054a033}}</ref> When treated with transition metal salts, it serves as a chelating ligand.<ref name=Musker/> |
The N-H centers can be replaced with many other groups. As a bis secondary amine, it condenses with [[aldehyde]]s to give bicyclic derivatives.<ref>{{cite journal|title=Reaction of 1,5-Diazacyclooctane with Aldehydes|author1=Billman, John H. |author2=Dorman, Linneaus C.|journal=Journal of Organic Chemistry|year=1962|volume=27|pages=2419–22|doi=10.1021/jo01054a033}}</ref> When treated with transition metal salts, it serves as a chelating ligand.<ref name=Musker/> |
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Revision as of 11:43, 8 January 2024
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| Names | |
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| Preferred IUPAC name
1,5-Diazocane | |
| Other names
DACO, octahydro-1,5-diazocine
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H14N2 | |
| Molar mass | 114.192 g·mol−1 |
| Appearance | colorless liquid |
| Boiling point | 78–80 °C (172–176 °F; 351–353 K) 16 Torr |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,5-Diazacyclooctane is an organic compound with the formula (CH2CH2CH2NH)2. It is a colorless oil. 1,5-Diazacyclooctane is a cyclic diamine.[1]
Synthesis and reactions
It is prepared in low yield by the alkylation of ammonia with 1,3-dibromopropane.[2]
The N-H centers can be replaced with many other groups. As a bis secondary amine, it condenses with aldehydes to give bicyclic derivatives.[3] When treated with transition metal salts, it serves as a chelating ligand.[1]
Related compounds
References
- ^ a b Musker, W. Kenneth (1992). "Coordination Chemistry of Bidentate Medium Ring Ligands (Mesocycles)". Coordination Chemistry Reviews. 117: 133–57. doi:10.1016/0010-8545(92)80022-J.
- ^ Daniel K. Mills; Ivan Font; Patrick J. Farmer; et al. (1998). 1,5-Diazacyclooctane, Pendant Arm Thiolato Derivatives and [N,N'-Bis(2-mercaptoethyl)-1,5-diazacyclooctanato]nickel(II). Inorganic Syntheses. Vol. 32. pp. 89–98. doi:10.1002/9780470132630.ch15.
- ^ Billman, John H.; Dorman, Linneaus C. (1962). "Reaction of 1,5-Diazacyclooctane with Aldehydes". Journal of Organic Chemistry. 27: 2419–22. doi:10.1021/jo01054a033.