Synthesis of 5,6-Diaminoacenaphthylene by Reduction of Sterically Crowded Nitro Groups with Sodium Dithionite

Authors

Amber J. Dood
Patrick A. Fisher
Christine L. Bodden
Luke J. Peterson
Kathryn A. Lindberg
Trevor A. Coeling
Douglas C. Yarbrough
Jason G. Gillmore, Hope CollegeFollow

Document Type

Article

Publication Date

12-3-2018

Publication Source

SynOpen

Volume Number

2

Issue Number

4

First Page

312

Last Page

315

Publisher

Georg Thieme Verlag

ISSN

2509-9396

Comments

This journal article is published under the Creative Commons license CC BY-NC-ND 4.0 (Attribution-NonCommercial-NoDerivatives)

Abstract

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.

Keywords

nitration, bromination, elimination, reduction, sodium dithionite

Recommended Citation

Repository citation: Dood, Amber J.; Fisher, Patrick A.; Bodden, Christine L.; Peterson, Luke J.; Lindberg, Kathryn A.; Coeling, Trevor A.; Yarbrough, Douglas C.; and Gillmore, Jason G., "Synthesis of 5,6-Diaminoacenaphthylene by Reduction of Sterically Crowded Nitro Groups with Sodium Dithionite" (2018). Faculty Publications. Paper 1471.
https://digitalcommons.hope.edu/faculty_publications/1471

Published in: SynOpen, Volume 2, Issue 4, December 3, 2018, pages 312-315. Copyright © 2018 Georg Thieme Verlag, Stuttgart.