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 - Článek v odborném periodiku
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
Grant CEP: GA ČR(CZ) GA16-08327S
Institucionální podpora: RVO:61388963
Klíčová slova: helicene(di)thiols * synthesis * single-molecule conductivity
Obor OECD: Organic chemistry
Impakt faktor: 4.354, rok: 2020
Způsob publikování: Omezený přístup
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.
Trvalý link: http://hdl.handle.net/11104/0304521