Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 11, Pages 5663-5668Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b00486
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Funding
- MEXT-Supported Program for the Strategic Research Foundation at Private Universities [S1201034]
- Toho University
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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 MAIM isomers at room temperature. The activation parameters for the racemization of the PPP and MMM isomers were determihed, and the structure of the triple [5]helicene was determined by X-ray crystallographic analysis.
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