Chemistry:2,3-Butanediamine
2,3-Butanediamine are organic compounds with the formula CH3CH(NH2)CH(NH2)CH3. Three stereoisomers exist, meso and a pair of enantiomers. These diamines form complexes with transition metals.[1]
Synthesis
2,3-Butanediamines can be prepared by hydrolyzing 2-ethoxy-4,5-dihydro-4,5-dimethylimidazole with barium hydroxide.[2] Alternative, it is produced by reduction of dimethylglyoxime with lithium aluminium hydride.[3] The meso and the d,l diastereomers can be separated by fractional crystallization of the hydrochlorides. The enantiomers have been resolved using tartrate salts.[4]
Reactions
In coordination chemistry, 2,3-butanediamine (abbreviated bn) has illuminates aspects of the stereochemistry. The structure of [Co(meso-2,3-butanediamine)2CO3]+ confirms the presence of the rarely observed axial methyl groups on each of the diamine-cobalt rings.[5]
Related compounds
- 1,2-Diaminopropane, chiral 1,2-diamine
- 1,2-Diaminocyclohexane, a 1,2-diamine that also exists as three stereoisomers
References
- ↑ Tsuchiya, Ryokichi; Uehara, Akira; Yoshikuni, Tadatsugu (1982). "Solid-phase thermal cis-trans isomerization of bis(diamine)chromium(III) complexes containing d,l-2,3-butanediamine, d,l-1,2-cyclohexanediamine, or d,l-2,4-pentanediamine". Inorganic Chemistry 21 (2): 590–594. doi:10.1021/ic00132a025.
- ↑ Harold Kohn and Sang Hun Jung. New stereoselective method for the preparation of vicinal diamines from olefins and cyanamide. Journal of the American Chemical Society 1983 105 (12), 4106-4108. doi:10.1021/ja00350a068.
- ↑ Hilleary, Christopher J.; Them, Theodore F.; Tapscott, Robert E. (1980). "Stereochemical studies on diastereomers of tris(2,3-butanediamine)cobalt(III)". Inorganic Chemistry 19: 102–107. doi:10.1021/ic50203a022.
- ↑ Dickey, F. H.; Fickett, Wildon; Lucas, H. J. (1952). "Stereoisomeric 2,3-Butanediamines, 3-Amino-2-butanols and 2,3-Dimethylethyleneimines; Stereochemistry of the Opening and Closing of the Imine Ring1". Journal of the American Chemical Society 74 (4): 944–951. doi:10.1021/ja01124a023. Bibcode: 1952JAChS..74..944D.
- ↑ Duesler, E. N.; Fe Gargallo, M.; Tapscott, R. E. (1982). "Structure of lel lel lel tris[(±)-2,3-butanediamine]-cobalt(III) chloride". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 38 (4): 1300–1303. doi:10.1107/S0567740882005585. Bibcode: 1982AcCrB..38.1300D.
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