Progress towards the modular synthesis of Roesky's tetradentate NacNac ligand, CH[C(R)N(CH2)2N(R')x]2-, R = CH3, C(CH3)3; R' (x = 2) = CH3, CH2CH3, CH(CH3)2, C6H5; R' (x = 1) = (CH2)5 using air-stable reagents is presented. Attempts to synthesize various assymmetric ethylenediamines from ethanolamine have met with varied success. Boc protected N-(2-aminoethyl)piperidine has been isolated, and evidence of BocNH(CH2)2NR2 (R = CH2CH3, CH(CH3)2) has been observed, although the compounds have not been isolated in pure form. Attempts to mesylate the monosubstituted "Nacac" appear to result in substitution at the "activated methylene" carbon. Progress towards the synthesis of a novel tetradentate HNacNac dervative will also be presented.

Modular synthesis of a tetradentate HNacNac ligand

251st National Meeting (2016)

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