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Synfacts 2010(4): 0411-0411
DOI: 10.1055/s-0029-1219602
DOI: 10.1055/s-0029-1219602
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag
Stuttgart ˙ New York
Helicene and Double Helicene
Contributor(s):Timothy M. Swager, Brett VanVellerZ. Wang, J. Shi, J. Wang, C. Li, X. Tian, Y. Cheng*, H. Wang*
Henan University, Kaifeng, Luoyang Normal University and Changchun Institute of Applied Chemistry, P. R. of China
Syntheses and Crystal Structure of Benzohexathia[7]helicene and Naphthalene Cored Double Helicene
Org. Lett. 2010, 12: 456-459
Henan University, Kaifeng, Luoyang Normal University and Changchun Institute of Applied Chemistry, P. R. of China
Syntheses and Crystal Structure of Benzohexathia[7]helicene and Naphthalene Cored Double Helicene
Org. Lett. 2010, 12: 456-459
Further Information
Publication History
Publication Date:
22 March 2010 (online)
Key words
helicenes - naphthalenes - McMurry reaction - thiophenes
Significance
A high-yield synthesis of three novel helicene compounds (3, 5 and 6) was developed. X-ray single-crystal structure analysis revealed multiple intermolecular short contacts and UV/Vis spectra indicate significant π-delocalization in double helicene 6, indicating potential in organic functional materials.
Comment
The efficient synthesis of 1 can be achieved in a total yield of 28% from 3-bromothiophene (J. Org. Chem. 2009, 74, 408).