2,3-Butanediamine Explained

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

Notes and References

1. 10.1021/ic00132a025 . 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 . 1982 . Tsuchiya . Ryokichi . Uehara . Akira . Yoshikuni . Tadatsugu . Inorganic Chemistry . 21 . 2 . 590–594 .
2. 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. .
3. 10.1021/ic50203a022 . Stereochemical studies on diastereomers of tris(2,3-butanediamine)cobalt(III) . 1980 . Hilleary . Christopher J. . Them . Theodore F. . Tapscott . Robert E. . Inorganic Chemistry . 19 . 102–107 .
4. 10.1021/ja01124a023 . Stereoisomeric 2,3-Butanediamines, 3-Amino-2-butanols and 2,3-Dimethylethyleneimines; Stereochemistry of the Opening and Closing of the Imine Ring¹ . 1952 . Dickey . F. H. . Fickett . Wildon . Lucas . H. J. . Journal of the American Chemical Society . 74 . 4 . 944–951 .
5. 10.1107/S0567740882005585 . Structure of lel lel lel tris[(±)-2,3-butanediamine]-cobalt(III) chloride . 1982 . Duesler . E. N. . Fe Gargallo . M. . Tapscott . R. E. . Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry . 38 . 4 . 1300–1303 . 1982AcCrB..38.1300D .