2-Bromo[6]helicene as a Key Intermediate for [6]Helicene Functionalization.

0488982 - ÚCHP 2019 RIV US eng J - Journal Article
Jakubec, Martin - Beránek, Tomáš - Jakubík, Pavel - Sýkora, Jan - Žádný, Jaroslav - Církva, Vladimír - Storch, Jan
2-Bromo[6]helicene as a Key Intermediate for [6]Helicene Functionalization.
Journal of Organic Chemistry. Roč. 83, č. 7 (2018), s. 3607-3616. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA ČR GA15-12719S
Institutional support: RVO:67985858
Keywords : helicene * racemization barrier * enantiomers
OECD category: Organic chemistry
Impact factor: 4.745, year: 2018

The synthesis of 2-bromo[6]helicene was revised and improved up to 51% yield. Its reactivity was thoroughly investigated, and a library of 17 different carbon, boron, nitrogen, phosphorus, oxygen and sulfur substituted derivatives was prepared. The racemization barrier for 2-bromo[6]helicene was determined, and the usage of enantiomers in the synthesis of optically pure helicenes was rationalized. The three most energy-demanding reactions using enantiomerically pure 2-bromo[6]helicene were tested in order to confirm the predicted enantiomeric excess.
Permanent Link: http://hdl.handle.net/11104/0283624