Synthesis of Racemic, Diastereopure, and Enantiopure Carba- or Oxa[5]-, [6]-, [7]-, and -[19]helicene (Di)thiol Derivatives

0519353 - ÚOCHB 2021 RIV US eng J - Journal Article
Nejedlý, Jindřich - Šámal, Michal - Rybáček, Jiří - Gay Sánchez, Isabel - Houska, Václav - Warzecha, Tomáš - Vacek, Jaroslav - Sieger, Ladislav - Buděšínský, Miloš - Bednárová, Lucie - Fiedler, Pavel - Císařová, I. - Starý, Ivo - Stará, Irena G.
Synthesis of Racemic, Diastereopure, and Enantiopure Carba- or Oxa[5]-, [6]-, [7]-, and -[19]helicene (Di)thiol Derivatives.
Journal of Organic Chemistry. Roč. 85, č. 1 (2020), s. 248-276. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA ČR(CZ) GA16-08327S
Institutional support: RVO:61388963
Keywords : helicene(di)thiols * synthesis * single-molecule conductivity
OECD category: Organic chemistry
Impact factor: 4.354, year: 2020
Method of publishing: Limited access
https://pubs.acs.org/doi/abs/10.1021/acs.joc.9b02965

A series of carba- or oxa[5]-, [6]-, [7]-, and[19]helicene (di)thiols was prepared. The Miyazaki-Newman-Kwart rearrangement of (dimethylcarbamothioyl)oxy (oxa)helicenes in a flow reactor or nucleophilic substitution of dichloro (oxa)helicenes with alkanethiolates were used in the sulfanylation step. Despite the high temperatures employed in this key step, no conformational scrambling was observed during the asymmetric synthesis of the diastereo- and enantiopure oxahelicenes. Single-molecule conductivity of the longest oxa[19]helicene dithiol derivative was studied by the scanning tunneling microscopy break-junction method.
Permanent Link: http://hdl.handle.net/11104/0304521