Interesting Products Derived from the Reactions of 2,3-Diamino-2,3-dimethylbutane

Article abstract of DOI:10.1021/jo00076a034

The diimine, N,N'-dibenzylidene-2,3-diamino-2,3-dimethylbutane (10), was successfully synthesized from 2,3-diamino-2,3-dimethylbutane (3) by reaction with excess benzaldehyde.The reaction of diimine 10 with permanganate/PTC at pH = 4.1 did not give corresponding dinitrone 11 but unexpectedly gave 3-benzoyl-4,4,5,5-tetramethyl-2-phenylimidazoline (13) in 45 percent yield.The imidazoline 13 was independently prepared by benzoylation of 4,4,5,5-tetramethyl-2-phenylimidazoline (9) which had been synthesized from diamine 3 and methyl benzimidate.The cyclic α-dinitrone,2,3-dihydro-2,2,3,3,5,6-hexamethylpyrazine 1,4-dioxide (4), synthesized from N,N'-dihydroxy-2,3-diamino-2,3-dimethylbutane (2) and 2,3-butanedione, underwent ozonolysis to yield the corresponding vicinal dinitro compound, 2,3-dimethyl-2,3-dinitrobutane (1), quantitatively.