Syntheses of Fused Thiophenes: [7]Helicene and Double Helicene Bearing Chiral Alkyl Chains

Author(s): Juanjuan Yang, Chunli Li, Zhihua Wang, Hua Wang.

Journal Name:Letters in Organic Chemistry

Volume 9 , Issue 10 , 2012

Abstract:

In this paper, an efficient synthesis of the two attractive fused thiophenes: [7]helicene (1) and double helicene (2) bearing chiral chains was developed via multi-step moisture sensitive reactions in ca. 10.5 % and ca. 6.0 % isolated yields, respectively, with dithieno[2,3-b:3',2'-d]thiophene (7) as a starting material. However, 1 and 2 showed no optical rotations due to the too weak contribution from chiral induction of the chiral chain, (S)-3,7-dimethyl-octyl group in the formation of helicenes.

Keywords: [7]helicene, chiral chain, double helicene, thiophene-based, synthesis

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Article Details

VOLUME: 9
ISSUE: 10
Year: 2012
Page: [706 - 710]
Pages: 5
DOI: 10.2174/157017812803901926