Synthesis of 5,6-Diaminoacenaphthylene by Reduction of Sterically Crowded Nitro Groups with Sodium Dithionite
This work was supported in part by: NSF CAREER (CHE-0952768), NSF REU (CHE-0243828 & CHE-0851194), NSF STEM-ENGINES URC (CHE-0629174), a Henry Dreyfus Teacher-Scholar Program award to J.G.G., an HHMI Scholar award to C.L.B. and J.G.G. by a grant to Hope College by the Howard Hughes Medical Institute through the Undergraduate Science Education Program, and the Hope College Chemistry Department’s Schaap Research Fellows program and Undergraduate Research Fund. The MU3C  cluster was supported by NSF MRI (CHE-0520704 & CHE-1039925).
Received: 09 November 2018
Accepted after revision: 12 November 2018
03 December 2018 (online)
5,6-Diaminoacenaphthylene was synthesized in four steps from acenaphthene. This seemingly simple molecule provides unique synthetic challenges because it is relatively difficult to reduce the nitro groups and the molecule contains a particularly reactive double bond. It was determined that the only feasible sequence for the synthesis was to nitrate acenaphthene, then brominate, eliminate, and finally selectively reduce. Several reduction methods were attempted before finding one that would completely reduce both nitro groups while leaving the double bond intact.
References and Notes
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