Synthesis of a Three-Bladed Propeller-Shaped Triple [5]Helicene

Three-bladed propeller-shaped triple [5]­helicene was synthesized using eliminative and oxidative photocyclization reactions, which proceeded in 37 and 63% yields, respectively. Chromatographic purification gave a mixture of diastereomers, and the PPM and PMM isomers were gradually converted to the...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 82; no. 11; pp. 5663 - 5668
Main Authors Saito, Hiromu, Uchida, Akira, Watanabe, Soichiro
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.06.2017
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
RACEMIZATION BARRIERS
HEXABENZOTRIPHENYLENE
PI-SYSTEMS
PHOTOCHEMISTRY
PHOTOCYCLIZATION
DERIVATIVES
DOUBLE HELICENE
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Summary:Three-bladed propeller-shaped triple [5]­helicene was synthesized using eliminative and oxidative photocyclization reactions, which proceeded in 37 and 63% yields, respectively. Chromatographic purification gave a mixture of diastereomers, and the PPM and PMM isomers were gradually converted to the thermodynamically more stable PPP and MMM isomers at room temperature. The activation parameters for the racemization of the PPP and MMM isomers were determined, and the structure of the triple [5]­helicene was determined by X-ray crystallographic analysis.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00486