Synfacts 2009(11): 1211-1211  
DOI: 10.1055/s-0029-1218093
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Chrysenes through an Unexpected Skeletal Rearrangement

Contributor(s): Timothy M. Swager, Rebecca R. Parkhurst
H. Isobe*, S. Hitosugi, T. Matsuno, T. Iwamoto, J. Ichikawa
Tohoku University, Sendai and University of Tsukuba, Japan
Further Information

Publication History

Publication Date:
22 October 2009 (online)

Significance

In the development of a method for the synthesis of [4]helicenes (J. Ichikawa et al. Angew. Chem. Int. Ed. 2008, 47, 4870), the authors discovered that they could obtain halogenated chrysene as a major product by extending the reaction time. The authors also show that further modification of chrysenes 3a-e is possible at the halogenated positions through lithiation-protonation to give the nonhalogenated derivatives and cross-coupling. The single crystals π-stack in one of three motifs shown above, while the non­halogenated analogue assumes a herringbone conformation.